Homework Organic

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Homework 1,\u160\'3f
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Student Name: ____________________________________
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14.09.2016 02:49 PM
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Homework 1,\u160\'3f
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Student Name: ____________________________________
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14.09.2016 02:49 PM
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1.\u160\'3f
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{\f0 \b1 \fs22 \cf1 \i0
Problem 11.26a
\par
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{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Draw the structural formula for (
}
{\f4 \b0 \fs18 \cf1 \i1
Z
}
}
)-But-2-en-1-ol
\par
}
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{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
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{\*\shppict {\pict \pngblip \picw1 \pich1 \picwgoal15 \pichgoal15
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\u160\'3f
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2.\u160\'3f
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{\f0 \b1 \fs22 \cf1 \i0
Problem 11.26b
\par
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}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Draw the structural formula for (
}
{\f4 \b0 \fs18 \cf1 \i1
R
}
}
)-butane-1,2,4-triol.
\par
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{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
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\u160\'3f
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3.\u160\'3f
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{\f0 \b1 \fs22 \cf1 \i0
Problem 11.26e
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Draw the structural formula for 2-chlorohex-3-yn-1-ol
\par
}
}
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{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
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\par
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\u160\'3f
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4.\u160\'3f
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{\f0 \b1 \fs22 \cf1 \i0
Problem 11.26g
\par
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}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Draw the structural formula for 2-ethoxypentane.
\par
}
}
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}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
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\par
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{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
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{\f0 \b1 \fs22 \cf1 \i0
5.\u160\'3f
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{\f0 \b1 \fs22 \cf1 \i0
Problem 11.26j
\par
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}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Draw the structure of 2-ethoxyethanol.
\par
}
}
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}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
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{\f4 \b0 \sb200 \fs18 \cf1 \i0
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9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
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\par
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}
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{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
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{\f0 \b1 \fs22 \cf1 \i0
6.\u160\'3f
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{\f0 \b1 \fs22 \cf1 \i0
Problem 11.27c
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Provide the alkene needed to synthesize the following by oxymercuration-
demercuration.
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
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\par
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{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
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{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
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{\f4 \b0 \sb200 \fs18 \cf1 \i0
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\par
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{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f0 \b1 \fs22 \cf1 \i0
7.\u160\'3f
}
}
{\f0 \b1 \fs22 \cf1 \i0
Problem 11.28
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Provide the alkene needed to synthesize each of the following by hydroboration-
oxidation.
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(a)
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
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\u160\'3f
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{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
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(b)
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{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
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\u160\'3f
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(c)
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\par
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{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
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{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
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\par
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{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
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(d)
\par
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e6da0bcb692dae6149a09176bc722e5587a114012d1581b750f0f64c7e7ea3a50ff00967cbdc5b8f627
9957dbef8e796e00d9b4bbb7beb64b9b5992685feeba1c8340135155ef6fad34eb57b9bdb986da04e5a
499c228fc4d79af883e37e8b6521b5d0ad66d5eec9daa54148f3d3838cb7e039f5a00f52a2be7e37df1
73c5ba85bddc36577696f14cb2a43b7ecd17073f36e219c7b126bdfd0b1452ebb5881919ce0d00605e5
baea3e2b5b1d458bd9adaadc5b5b6ec24aeac5642ebfc5b774780723e6e9900d74358be20cdab69faaa
eeff0043b9512ed0398a4f91f3ec0b2b9ff72b6a800a28a2800ae6759b036faada369170f617da8ce56
76891591d550967743c1601400dd72541c8e2ba6ac6b6db7de2abbb8e0a69f08b543e923e2493ff001d
10feb4018eff000d744bdb95bad6e6bfd6ae14e435f5c92a3e88bb540f6c5747a768da5e91188f4ed3a
d6d17d208553f90abd450014514500417d670ea161716570a1e0b889a2914f756183fcea9787aee5bcd
0eddae5835d45badee08046658c947383d895247b115a9582f6bace9da9decba5dad8dd5b5dbacccb73
7af098e4da15b0044e3042a9edce7d68037a8ac3fb578abfe80da37fe0da5ff00e46a3ed5e2affa0368
dff83697ff0091a8036279a3b6b79279982451a97763d000324d6778721913448679d192e2ecb5d4a8d
d55a43bb69ff7410bff0001aced423f10ea7632595ee9da55bd94b8172f1df493b18b20ba84f2172597
2bd7be79e87a55219415e8471400b451450014514500145145001451450015cf3dc9d0757583605b1bb
9018d5100fde3139544505dd8b12eec70a17f1ae86a86af61fda162f1aa832807666468c1ff0064b2fc
c14e0640eb8a00bcacaca194820f70696b8bb3d52fb4e9a6d1b45d35b589eccafdae5332dadbc0c5462
28c60e30b8f940e3b9c926ac9f1c446c6da51612c774da9c3a65d5a4ce15ede49180c923218608231c1
1dc5007574564eb7adff00634ba4a7d9fcefed0bf4b3cefdbe5ee576ddd0e7ee74e3af5ad6a0028a28a
0028a28a0028a28a00e134ed5acfc19abebb69aec86d22bdbf7beb5ba78d8c732baae5770046e523183
ce318cd73babdacdaa34fac8173636dabf8834d8ed5b67972ec4c279c030e09249191d00c8af5da2803
cebc41a0cda5eabe169e4d7b56d4036b51279579246c83f7721dc36a29cf18ebdcd7a2d145007ffd9}}
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f0 \b1 \fs22 \cf1 \i0
8.\u160\'3f
}
}
{\f0 \b1 \fs22 \cf1 \i0
Problem 11.29a
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Using the reagents below, list in order (by letter, no period) those necessary to
prepare 1-butanol from 1-butene.
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
Note: Not all spaces provided may be needed. Type \ldblquote na\rdblquote in any
space where you have no reagent.
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\f4 \b1 \fs18 \cf1 \i0
a.
}
}
Br
}
{\f4 \b0 \fs18 \cf1 \i0
{\f4 \sub \strike0 \ul0 \b0 \sa0 \sb0 \fs18 \cf1 \i0
2
}
}
, heat, light
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b1 \fs18 \cf1 \i0
b.
}
}
Br
}
{\f4 \b0 \fs18 \cf1 \i0
2
}
}
, dark
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b1 \fs18 \cf1 \i0
c.
}
}
NaI(S
}
{\f4 \b0 \fs18 \cf1 \i0
N
}
}
2)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b1 \fs18 \cf1 \i0
d.
}
}
BH
}
{\f4 \b0 \fs18 \cf1 \i0
3
}
}
: THF (hydroboration)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b1 \fs18 \cf1 \i0
e.
}
}
HI
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b1 \fs18 \cf1 \i0
f.
}
}
NH
}
{\f4 \b0 \fs18 \cf1 \i0
4
}
}
NO
}
{\f4 \b0 \fs18 \cf1 \i0
3
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b1 \fs18 \cf1 \i0
g.
}
}
H
}
{\f4 \b0 \fs18 \cf1 \i0
2
}
}
O
}
{\f4 \b0 \fs18 \cf1 \i0
2
}
}
/OH
}
{\f4 \b0 \fs18 \cf1 \i0
{\super \f4 \strike0 \ul0 \b0 \sa0 \sb0 \fs18 \cf1 \i0
-
}
}
(oxidation)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0 {
\clpadt40 \clpadft3 \clpadb40 \clpadfb3 \clpadl40 \clpadfl3 \clpadr40 \clpadfr3
\clbrdrt \clbrdrl \trql \cellx3583
\clbrdrt \trql \cellx7166
\clbrdrt \clbrdrr \trql \cellx10749
\intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Step #1
\cell
}
}
}\f4 \li0 \strike0 \ul0 \b0 \chcbpat2 \sa0 \ql \sb0 \fs18 \ri0 \cf1 \nosupersub \i0
\intbl \intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Step #2
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Step #3
\cell
}
}
\intbl \row }
\clbrdrb \clbrdrl \trql \cellx3583
\clbrdrb \trql \cellx7166
\clbrdrb \clbrdrr \trql \cellx10749
\intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
{\chbrdr \brdrw20 \brdrcf1 \brdrs \f4 \b1 \chcbpat2 \fs18 \cf1 \i0
\
u160\'3f\u160\'3f\u160\'3f\u160\'3f\u160\'3f\u160\'3f\u160\'3f\u160\'3f\u160\'3f\u1
60\'3f\u160\'3f\u160\'3f\u160\'3f\u160\'3f\u160\'3f\u160\'3f\u160\'3f\u160\'3f\u160
\'3f\u160\'3f\u160\'3f\u160\'3f\u160\'3f\u160\'3f\u160\'3f\u160\'3f\u160\'3f\u160\'
3f\u160\'3f\u160\'3f
\cell
}
}
}
}
}
}\f4 \chbrdr \ul0 \b1 \chcbpat2 \ql \ri0 \i0 \li0 \strike0 \sa0 \sb0 \fs18 \cf1
\nosupersub \intbl \intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\cell
}
}
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\cell
}
}
}
}
}
\nosupersub \intbl \row }}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f0 \b1 \fs22 \cf1 \i0
9.\u160\'3f
}
}
{\f0 \b1 \fs22 \cf1 \i0
Problem 11.29c
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
prepare 1-butanol from 2-chlorobutane.
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\f4 \b1 \fs18 \cf1 \i0
a.
}
}
(CH
}
{\f4 \b0 \fs18 \cf1 \i0
3
}
}
)
}
{\f4 \b0 \fs18 \cf1 \i0
3
}
}
COK, (CH
}
{\f4 \b0 \fs18 \cf1 \i0
3
}
}
)
}
{\f4 \b0 \fs18 \cf1 \i0
3
}
}
COH
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b1 \fs18 \cf1 \i0
b.
}
}
Br
}
{\f4 \b0 \fs18 \cf1 \i0
2
}
}
, dark
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b1 \fs18 \cf1 \i0
c.
}
}
HBr, ROOR
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b1 \fs18 \cf1 \i0
d.
}
}
NH
}
{\f4 \b0 \fs18 \cf1 \i0
4
}
}
NO
}
{\f4 \b0 \fs18 \cf1 \i0
3
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b1 \fs18 \cf1 \i0
e.
}
}
HI
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b1 \fs18 \cf1 \i0
f.
}
}
OH
}
{\f4 \b0 \fs18 \cf1 \i0
{\super \f4 \strike0 \ul0 \b0 \sa0 \sb0 \fs18 \cf1 \i0
-
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b1 \fs18 \cf1 \i0
g.
}
}
NaI(S
}
{\f4 \b0 \fs18 \cf1 \i0
N
}
}
2)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0 {
\intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Step #1
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Step #2
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Step #3
\cell
}
}
\intbl \row }
\intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\cell
}
}
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\cell
}
}
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\cell
}
}
}
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f0 \b1 \fs22 \cf1 \i0
10.\u160\'3f
}
}
{\f0 \b1 \fs22 \cf1 \i0
Problem 11.32e
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
prepare cyclohexylmethanol from 1-bromo-1-methylcyclohexane.
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\f4 \b1 \fs18 \cf1 \i0
a.
}
}
}
{\f4 \b0 \fs18 \cf1 \i1
t-
}
}
BuOK,
}
{\f4 \b0 \fs18 \cf1 \i1
t-
}
}
BuOH
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b1 \fs18 \cf1 \i0
b.
}
}
HBr (no peroxides)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b1 \fs18 \cf1 \i0
c.
}
}
PBr
}
{\f4 \b0 \fs18 \cf1 \i0
3
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b1 \fs18 \cf1 \i0
d.
}
}
SOCl
}
{\f4 \b0 \fs18 \cf1 \i0
2
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b1 \fs18 \cf1 \i0
e.
}
}
HCl
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b1 \fs18 \cf1 \i0
f.
}
}
HA, heat
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b1 \fs18 \cf1 \i0
g.
}
}
(1) BH
}
{\f4 \b0 \fs18 \cf1 \i0
3
}
}
:THF, (2) H
}
{\f4 \b0 \fs18 \cf1 \i0
2
}
}
O
}
{\f4 \b0 \fs18 \cf1 \i0
2
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0 {
\intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Step #1
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Step #2
\cell
}
}
\intbl \row }
\intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\cell
}
}
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\cell
}
}
}
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f0 \b1 \fs22 \cf1 \i0
11.\u160\'3f
}
}
{\f0 \b1 \fs22 \cf1 \i0
Problem 11.35g
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Draw the structure of the product(s) that would be formed when cyclopentanol reacts
with sulfuric acid at 140\u176\'3fC:
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f0 \b1 \fs22 \cf1 \i0
12.\u160\'3f
}
}
{\f0 \b1 \fs22 \cf1 \i0
Problem 11.33a
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
What compounds would you expect to be formed when the following compound is
refluxed with excess concentrated hydrobromic acid?
\par
}
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
89504e470d0a1a0a0000000d49484452000000500000002a080300000013762c3800000300504c54452
31f2034323336343646464849494b5455576263656f70727475777c7d7f81828587898c8d8f92939598
9a9c9f9fa1a4a7a9acacaeb1b9bbbdc3c5c7c7c8cad1d2d4d4d5d6dfe0e1e1e2e3eff0f0f0f0f1fffff
f231f20231f20231f20231f200000000000000000000000000000000000000000000000000000000000
00000000000000000000000000000000000000000000000000000000000000000000000000000000000
00000000000000000000000000000000000000000000000000000000000000000000000000000000000
00000000000000000000000000000000000000000000000000000000000000000000000000000000000
00000000000000000000000000000000000000000000000000000000000000000000000000000000000
00000000000000000000000000000000000000000000000000000000000000000000000000000000000
00000000000000000000000000000000000000000000000000000000000000000000000000000000000
00000000000000000000000000000000000000000000000000000000000000000000000000000000000
00000000000000000000000000000000000000000000000000000000000000000000000000000000000
00000000000000000000000000000000000000000000000000000000000000000000000000000000000
00000000000000000000000000000000000000000000000000000000000000000000000000000000000
00000000000000000000000000000000000000000000000000000000000000000000000000000000000
00000000000000000000000000000000000000000000000000000000000000000000000000000000000
00000000000000000000000000000000000000000000000000000000000000000000000000000000000
00000000000000000000000000000000000000000000000000000000000000000000000000000000000
00000000000000000000000000000000000000000000000000000000000000000000000000000000000
00000000000000000000000000000000000000000f8e40db8000000097048597300000b1300000b1301
009a9c18000001314944415478daed966b6f83201486b929628db69a651ff6ffffdd2a5509de40a66bb
7d479c125264b16cf17c8e1f5010eaf287c03fb060207f0001ec03f009285bcca9a0eb911f9351087b3
e9e65d7b0cd592e29d56c851d28fa82b7fdda786950a869948a0aa7d8035609f2deb7bbb00bb471ef53
d5b98b4b6d7b007a167f04ae4c223762015e569684b40d7716586136a3d658d3c22e870ca82786b389d
b667dfea4393714a5c299592b989b1cce8c2b67ba19fb856638b2b7c710066aaaeb41b3b80b41cb8708
63708d974008e3fa375d65d7e96adbde9d09f186b4638056ade84c17ce9c3d1d34bc231d014c529828b
e688f016e11350de9c78f92a30bc0ac22dc22f609deb88ad5aeea1b009ef409d7dcfbf1232c7416913d
e8129b8c00d2fbe29846713c2e3efeb001ec07f01fc00d1e9760fc4d694060000000049454e44ae4260
82}}
\par
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
\u160\'3f
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0 {
\intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d49484452000000140000001404030000007fa7003e00000030504c5445f
fffffcbcbcb3f3f3f3434347f7f7fc0c0c0808080121212989898edededd5d5d5676767000000000000
000000000000c0031c84000000097048597300000b1300000b1301009a9c18000000824944415478da6
360200098815844369ee3010303130303879291b2520358a27b010303d70e06061606c6f5c71818bebd
16f800e42480a4d81c806aff7d0031ff3f0032591d404c960090090873ffb3df00d28ccf3e303130098
084181540841588b95800a8f67f20c80ad10f20371c7e649729f2f90088f9e7e74791eb0b18080300dd
ee1e632502c8810000000049454e44ae426082}}
\cell
}
}
}\f4 \li0 \b0 \chcbpat2 \ql \fs18 \ri0 \cf1 \i0 \intbl \intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
2 molecules of CH
}
{\f4 \b0 \fs18 \cf1 \i0
3
}
}
CH
}
{\f4 \b0 \fs18 \cf1 \i0
2
}
}
Br
\cell
}
}
}\f4 \sub \ul0 \b0 \chcbpat2 \ql \ri0 \i0 \li0 \strike0 \sa0 \sb0 \fs18 \cf1
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0 {
\intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d49484452000000140000001404030000007fa7003e00000030504c5445f
000000000000c0031c84000000097048597300000b1300000b1301009a9c18000000824944415478da6
360200098815844369ee3010303130303879291b2520358a27b010303d70e06061606c6f5c71818bebd
ee1e632502c8810000000049454e44ae426082}}
\cell
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
CH
}
{\f4 \b0 \fs18 \cf1 \i0
3
}
}
Br and CH
}
{\f4 \b0 \fs18 \cf1 \i0
3
}
}
CH
}
{\f4 \b0 \fs18 \cf1 \i0
2
}
}
Br
\cell
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0 {
\intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d49484452000000140000001404030000007fa7003e00000030504c5445f
000000000000c0031c84000000097048597300000b1300000b1301009a9c18000000824944415478da6
360200098815844369ee3010303130303879291b2520358a27b010303d70e06061606c6f5c71818bebd
ee1e632502c8810000000049454e44ae426082}}
\cell
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
CH
}
{\f4 \b0 \fs18 \cf1 \i0
3
}
}
Br and CH
}
{\f4 \b0 \fs18 \cf1 \i0
3
}
}
CH
}
{\f4 \b0 \fs18 \cf1 \i0
2
}
}
OH
\cell
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0 {
\intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d49484452000000140000001404030000007fa7003e00000030504c5445f
000000000000c0031c84000000097048597300000b1300000b1301009a9c18000000824944415478da6
360200098815844369ee3010303130303879291b2520358a27b010303d70e06061606c6f5c71818bebd
ee1e632502c8810000000049454e44ae426082}}
\cell
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
2 molecules of CH
}
{\f4 \b0 \fs18 \cf1 \i0
3
}
}
Br
\cell
}
}
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f0 \b1 \fs22 \cf1 \i0
13.\u160\'3f
}
}
{\f0 \b1 \fs22 \cf1 \i0
Problem 11.34b
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Draw the structure of the product that would be formed when 1-butanol reacts with
sodium hydride, then 1-bromoethane.
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f0 \b1 \fs22 \cf1 \i0
14.\u160\'3f
}
}
{\f0 \b1 \fs22 \cf1 \i0
Problem 11.34c
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
methanesulfonyl chloride and base. Remember to draw out the double bonds between
the sulfur and oxygen on your drawing.
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f0 \b1 \fs22 \cf1 \i0
15.\u160\'3f
}
}
{\f0 \b1 \fs22 \cf1 \i0
Problem 11.34d
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Draw the structure of the final product that would be formed from the following
reaction. Draw just the main product. Do not draw the leaving group.
\par
}
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0 {
\clbrdrt \clbrdrb \trql \cellx5374
\intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
ffd8ffe000104a46494600010101006000600000ffe1002245786966000049492a00080000000100005
10400010000000000000000000000ffdb004300080606070605080707070909080a0c140d0c0b0b0c19
2ffdb0043010909090c0b0c180d0d1832211c2132323232323232323232323232323232323232323232
32323232323232323232323232323232323232323232323232323232ffc0001108004400d2030122000
21101031101ffc4001f0000010501010101010100000000000000000102030405060708090a0bffc400
b5100002010303020403050504040000017d01020300041105122131410613516107227114328191a10
82342b1c11552d1f02433627282090a161718191a25262728292a3435363738393a434445464748494a
535455565758595a636465666768696a737475767778797a838485868788898a92939495969798999aa
60708090a0bffc400b51100020102040403040705040400010277000102031104052131061241510761
711322328108144291a1b1c109233352f0156272d10a162434e125f11718191a262728292a353637383
93a434445464748494a535455565758595a636465666768696a737475767778797a8283848586878889
6d7d8d9dae2e3e4e5e6e7e8e9eaf2f3f4f5f6f7f8f9faffda000c03010002110311003f00f7fa28a280
0a28a2800a28a2800a28a2800a28a2800a28a2800a28a2800a28a2800a28a2800a28a28032bc47a94da
56873dd5baa99b7c7121619552f22a0623d17764fb03546ca6d4b4df12c3a55dea326a50dddacb70b24
b1223c2d1b202bf228054f99c6464153c9cf1bf716f0dddbc96f7112cb0caa51d1c64303d4115c67c3c
960ba93c432ada2c52da6a93582c866965668e3c6d05a46623ef1e0607b50076f451450014514500145
14500145145001451450014514500145145001451450014514500145145001451450015952f89349875
23a7bdde275711b111b98d1ce30ad201b558e47ca483c8f5ad5ae52dad759d3a5bcd361d3639e1b9bf7
ba5be964431aa3c9bd832121b72e4a80011c2f23b006d47aee9b2c76b225ce52eae5ed213b1be69537e
e5e9c63cb7e4f1c75e46746bceedbc31ac69eba65f493dd4ab6bab5dddc962f2c2218a36fb41575380d
93bd3ab1c6f39031c74ba55dde6bd6f24f24d3e9d2c32b4124101575dcbce419220dc823a81ea320824
036ee2e21b4b696e6e2548a0890bc9239c2aa819249f402b89f8691bc4be253223c6d71accf751a488c
8fe53e3631560080707191daba3bfd2ee26d26fedcdd3df99eda4896def022c4e48e031440c01e9c1e8
4d63f85a3bb9df5354bcba8ad13cb863135d4375710ca85bcc52e37fcb82980e4b7dee066803afacabf
f12693a6de7d96eee8a4800672b13ba440f4323282b183fed1152ff675d7fd06afbfef883ff8dd61cf6
9ac69d7dada58e991de8d5a513457123a7970b79291ed95490cca3667e5072091c75a00e92cefadb508
9e5b593cc44964858e08c3a31461cfa3291562b17c316173a6e9b730dd461247bfbb994023051e77653
c138ca9071db35b54005145140051451400514564c5e25d1e7be1691dea1766d88fb488e4619caac98d
acc31ca8248a00d6a28a2800a28a2800a2a2b8b982d2ddee2e668e18631b9e49182aa8f524d53d3b5dd
3b5491a2b59cf9aa33e54b1b46e57fbc1580254f661c1f5a00d1a28a2800a28a2800a28a2800a28a280
11943295600a918208e08a82cac2cf4db55b6b0b482d6dd492b141184404f2700715628a002b82f861f
f003377fd8c577ffb2d751e23d4a6d2b439eeadd54cdbe3890b0caa979150311e8bbb27d81ac3d034d6
f0b78964d292e1eee1d5967d4a592445574983461bee8036b6f18e382a7ae7800ec68a28a0028a28a00
28a28a002b32fb5cb6b4b9fb1c2925e5f90185adb80ce01ce0b13c22f07962071c64d4fa859dc5ea245
15f4969167f7a6151e638f40c7eefb9033e8453ec74fb4d36dfc8b3816242771c7258f72c4f2c7dce4d
00658d1ef356f9f5e990c07a69f6cc7c9c7a48dc193bf1c2ffb2719ad69acad6e2cdace6b6864b665da
61640508f4c74c54f4500619b0d4b48f9b4b94de5a0ff972b990ee5ffae729e7fe02d91eea2ae69dacd
9ea4ef0c6cf15dc60196d675d92c7db257b8c838619071c135a154b50d2acf544417316648cee8a6462
92447d558723f0ebde802ed62cbaf1b99dad74583edf329db24dbb6dbc279cee93b918fbab93eb8ce69
9fd817575fb9d57579ef6c978580208bcc1c7fad65fbfdf81b5483ca9ada8a28e0892286348e341b551
1400a3d001d28032adf420f3a5dead3fdbeed0ee40cbb6184ffd338f903fde396f7ab9a869767aa44a9
770862877472292af1b7aab0e54fb835728a00c2f3358d17fd6abead623fe5a22817318f7518120ebc8
c3703863cd4d79e26d26cf475d51ee4c96eefe546b12169249338f2d500c97c8236e323073d2b5eb8ff
183a587883c31abde10ba65a5cccb71237dd85a48caa3b7a007232781ba803474df165adfea29a75c59
6a1a6de4aa5e18afe109e701d761048247523391e957b43d66df5fd263d46d525486479102ca006ca3b
21e848eaa7bf4ae6bc4d7d69ac6bde19d3f4cb88ae6f62d452f1cc0e1bc98155b7b311d036428cf5cfb
565f81f4ef12cfe14825d3fc456b696ad7173b20934df3597f7f2672de60ce4e4f4ef401dce85acdbf8
8344b4d5ad125482e937a2ca0060338e402476f5ad1ae4fe197fc936d0ffebdff00f6635d6500213804
804fb0ef589fdbba8ffd0a7acffdfdb3ff00e3f5b9450061ff006eea3ff429eb3ff7f6cfff008fd1fdb
ba8ff00d0a7acff00dfdb3ffe3f5b9450073f71ab5e5ddbc96f71e0ed5a5865528e8f25990c0f50479f
5474cff894492cb67e0dd744b2801a496f2de56c0e8a19ee490bc9e071ed478b758974fd6f4bb53adff
64db4f6d7523c9b233be4430ec5f9d4ff007db81c9ce3ae08e72e3c4de2b68e3b3795ac6ee37b59ee24
10a36d4b8920458f0571c33cebebfba1cf3401daff006eea3ff429eb3ff7f6cfff008fd1fdbba8ff00d
0a7acff00dfdb3ffe3f5b3123470a23c8d232a805d80058fa9c71cfb53e8030ff00b7751ffa14f59ffb
fb67ff00c7eb1ecbc5bab4be351a33e8777f669137bbb987759f1c0731c8e083db3b4fd7ad7694d48d2
32c51154b1dcdb46327d4d003a8a28a0028a28a0028a28a0028a28a0028a28a0028a28a0029b24692c6
d1c88ae8c30cac3208f4228a2802b58695a7696aeba7d85ada2b9cb0b785630c7d4e00cd4b6d6b6f650
082d608a085492238902a824924e071c924fd4d1450016b6b6f656d1db5a4115bc118c2451204551e80
0e054d45140051451400514514015e4b1b6975082f9e3cdcc11bc51bee3f2ab952c31d39d8bf97d692d
ec2dad6e6e6e6246f3ae5834aececc4e0600192700738030393c7268a2802cd14514005145140051451
401fffd9}}
\cell
}
}\f4 \li0 \b0 \chcbpat2 \fs18 \ri0 \cf1 \i0 \qc \intbl \intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
intermediate
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
product
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
ffd8ffe000104a46494600010101006000600000ffe1002245786966000049492a00080000000100005
10400010000000000000000000000ffdb004300080606070605080707070909080a0c140d0c0b0b0c19
2ffdb0043010909090c0b0c180d0d1832211c2132323232323232323232323232323232323232323232
32323232323232323232323232323232323232323232323232323232ffc000110800440037030122000
21101031101ffc4001f0000010501010101010100000000000000000102030405060708090a0bffc400
b5100002010303020403050504040000017d01020300041105122131410613516107227114328191a10
82342b1c11552d1f02433627282090a161718191a25262728292a3435363738393a434445464748494a
535455565758595a636465666768696a737475767778797a838485868788898a92939495969798999aa
60708090a0bffc400b51100020102040403040705040400010277000102031104052131061241510761
711322328108144291a1b1c109233352f0156272d10a162434e125f11718191a262728292a353637383
93a434445464748494a535455565758595a636465666768696a737475767778797a8283848586878889
0a28a2800a28a2800a28a2800a28a2800a28a2800a28a2800a28a2800a2b0bc5ff0068ff0084764f23c
ed9e741f68f273bfecfe6af9b8c73f73774e719ae3aedf4c5d4f46ff8436dade4886a5115292f9764ef
e45ce42950d8603ef10bfddcf3d003d3a8ae1fc3bacfd82f75d8756315bea175ab9448e0f3268c37916
ea3e7d83032c832c00cb01e958f65f61fb1e9bf61d9ff00097f9b17f6a633e77fd37f37bedc6edb9e3e
e6ded401ea145791787eeaeb48b6d00379ce2dbc3371796f2088c84aba5bb6dc646e2aeadc647054645
765e07d6aeb5687528aeaf52f0dadc2ac53068d8bc6d123024c6aaa46e2c01031c639c66803aba28a28
0286a37f73646316fa45edfefce4db3c2bb31ebe6489d7db3d2a97f6eea3ff00429eb3ff007f6cff00f
8fd6e51401c7eae6e7599ac24b9f0c6bea2cae16e11125b1c33a90549ccc48c11d548382c338241d4fe
ddd47fe853d67fefed9fff001fadca28030ffb7751ff00a14f59ff00bfb67ffc7e8feddd47fe853d67f
efed9ff00f1fadca28038ff000af8a754d5b5cd434cbbd2ae160b5cedbe6f2f04e7fd5b6c665de3bed6
edc85a2bae8e348a311c68a88bc0551803f0a2801d45145001451450014514500145145007ffd9}}
\cell
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
\u160\'3f
\par
}
}
final
\par
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
}
product
\cell
}
}
}\f4 \li0 \strike0 \ul0 \b0 \chcbpat2 \sa0 \sb0 \fs18 \ri0 \cf1 \nosupersub \i0 \qc
\intbl \row }}
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
\u160\'3f
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f0 \b1 \fs22 \cf1 \i0
16.\u160\'3f
}
}
{\f0 \b1 \fs22 \cf1 \i0
Problem 11.34f
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\f4 \b0 \fs18 \cf1 \i1
p-
}
}
toluenesulfonyl chloride, then base followed by KI. Draw just the main product. Do
not draw the leaving group.
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f0 \b1 \fs22 \cf1 \i0
17.\u160\'3f
}
}
{\f0 \b1 \fs22 \cf1 \i0
Problem 11.34g
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
sulfuric acid at 140\u176\'3fC.
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f0 \b1 \fs22 \cf1 \i0
18.\u160\'3f
}
}
{\f0 \b1 \fs22 \cf1 \i0
Problem 11.34l
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Draw the structure for the product of the following reaction. If more than one
product can reasonably be conceived from the reaction, draw the major product.
\par
}
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0 {
\intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
ffd8ffe000104a46494600010101006000600000ffe1002245786966000049492a00080000000100005
10400010000000000000000000000ffdb004300080606070605080707070909080a0c140d0c0b0b0c19
2ffdb0043010909090c0b0c180d0d1832211c2132323232323232323232323232323232323232323232
32323232323232323232323232323232323232323232323232323232ffc0001108002400a2030122000
21101031101ffc4001f0000010501010101010100000000000000000102030405060708090a0bffc400
b5100002010303020403050504040000017d01020300041105122131410613516107227114328191a10
82342b1c11552d1f02433627282090a161718191a25262728292a3435363738393a434445464748494a
535455565758595a636465666768696a737475767778797a838485868788898a92939495969798999aa
60708090a0bffc400b51100020102040403040705040400010277000102031104052131061241510761
711322328108144291a1b1c109233352f0156272d10a162434e125f11718191a262728292a353637383
93a434445464748494a535455565758595a636465666768696a737475767778797a8283848586878889
0a2a2babab7b2b692e6ee78e08231b9e595c2aa8f524f02b13fb4b54d6be5d1e1fb1d99ff9885dc6773
8ff00a6511c13fef3e0742030a00d2d4f58b1d22247bb9b0f212b1428a5e599bd11172cc7e829da76ab
65ab4066b2b859554ed75c1578dbfbaea7055bd8806a1d3743b3d32479d0493de4a312de5c36f9a41e8
5bb0ff6461476029ba8e836b7f38bb4692d35041b52f2d885900f43c10ebfecb023da803528ae7ffb5e
ff0046f935e80496c3a6a56884c607fd358f968fea372f7257a56ec3345710a4d04a92c5228647460ca
c0f4208ea2801f4514500145159fa9eb565a518e39dd9ee65cf936b0a992697fdd41ce3d4f41dc8a00d
0ac6bcf1568d6378d6d3ddfcd19c4f2246cf15b9ede6b80563ff008111507d8757d6fe6d4a56d36c4ff
cb95b49fbe71ff4d255e9feec7ff7d915b369656b6168969696f1416e830b14681547e0280264759115
d1832b0c8607208a5ac17d026d35da7f0f4e96793b9ac6404dac87be1473193ea9c772ad53597882292
e92c35181f4ed41b8586620acbff5ca41f2bfae06180eaa2803628a28a0028a28a0028a28a002b0a5f1
0b5e4cf6ba0db8d426462b25c16db6d09ee1a4c1dc47f75327d76f5ad0d4b4bb6d5a1482f3cc68036e7
89642ab2fb3e3ef2ffb2783df356a2863b7852186348e24015111405503a000741401916be1e57b98ef
b58b83a95ec677465d76c301ff00a671e4853fed1cb7fb58e2b6a8a2800a28a2800ac29bc3c6d667bbd
0ae469f3bb16921dbbada627aee8f2304ff00794a9f5cf4adda280312dbc4223b98ecb58b63a6de4876
c7bdf74139f48e4c004ffb2c15bfd9c735a77b7d6ba75abdd5edc456f027de92460a07e7de9f736b6f7
b6d25b5d411cf04836bc72a86561e841eb59763e17d32c2ed6e55269e48cffa3fdaa66985b0c748c313
b7bf239e719c0000041f6bd635ce2c227d2ec4ff00cbddcc7fbf907fd3389bee7d6419ff0063bd68e99
a359694246b78d9a797066b8958bcb29ff69cf27d8741d80157e8a0028a28a002abded8daea36af6b7b
6f15c40ff7a3914303f9f7ab1450073ff63d634439d3e46d4ec47fcba5ccbfbf8c7fd3395bef7fbb273
fed8e9525eebb77fdaefa5693a725edd4312cd70d35c7931421b3b54b056258ed3c05e9c922b72b9abb
b2d534af115e6b1a65926a115fc31473db99c45223c65b0ca48c1521b904820818ce780017c5ebe5598
92c248aea5d4974db8b77719824285f39190c300104750c3a74ad25d60378a1f45f24e52c96efcdddea
ec9b718ff6739cd73175e11bed4e3827d4eded269aeb5a4bfbcb6243c71c2b118d53e61872142e4e064
93dab4f4df0bdbe91e349f51d3b4fb3b3b0974e480adb46b1ee9048cc72aa076239a00e9e8a28a0028a
28a0028a28a0028a28a0028a28a0028a28a0028a28a0028a28a0028a28a0028a28a0028a28a0028a28a
00fffd9}}
\cell
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
ffd8ffe000104a46494600010101006000600000ffe1002245786966000049492a00080000000100005
10400010000000000000000000000ffdb004300080606070605080707070909080a0c140d0c0b0b0c19
2ffdb0043010909090c0b0c180d0d1832211c2132323232323232323232323232323232323232323232
32323232323232323232323232323232323232323232323232323232ffc0001108001a002c030122000
21101031101ffc4001f0000010501010101010100000000000000000102030405060708090a0bffc400
b5100002010303020403050504040000017d01020300041105122131410613516107227114328191a10
82342b1c11552d1f02433627282090a161718191a25262728292a3435363738393a434445464748494a
535455565758595a636465666768696a737475767778797a838485868788898a92939495969798999aa
60708090a0bffc400b51100020102040403040705040400010277000102031104052131061241510761
711322328108144291a1b1c109233352f0156272d10a162434e125f11718191a262728292a353637383
93a434445464748494a535455565758595a636465666768696a737475767778797a8283848586878889
6d7d8d9dae2e3e4e5e6e7e8e9eaf2f3f4f5f6f7f8f9faffda000c03010002110311003f00f7fa8cdc42
2e56d8cd189dd0c8b1161b8a82012075c02c067dc7ad495caeb363abdc78db4e9f4b9e3b509a75c23dc
4d68d3c7cc90909c3ae18e3239e8a78f400d693c4ba0c52c11c9ade9a925c2abc2ad7680caadf74a8cf
20f623ad6a578d5ae9dabc5a2c9a6bc77364b7de1eb3b470fa35c5c9660260ca190811b0de33bb3f787
4c577fe0787511a34f73aaa5ec3793ddce5adee666710a895f62a678dbb718238231db1401d35145140
14f51b8beb7890d858a5db9386569c45b47ae707359dfda5e22ffa17a0ff00c180ff00e22b768a00c2f
ed2f117fd0bd07fe0c07ff1147f69788bfe85e83ff0603ff88adda280389d035ef125e78baeac27d352
4d21725aec4c1becf27cd98f7000498200c0195cf24d76d4631d28a00fffd9}}
\par
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
\u160\'3f
\cell
}
}
}
\intbl \intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
\cell
}
}\f4 \li0 \b0 \chcbpat2 \fs18 \ri0 \cf1 \i0 \qc \intbl \row }}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f0 \b1 \fs22 \cf1 \i0
19.\u160\'3f
}
}
{\f0 \b1 \fs22 \cf1 \i0
Problem 11.35b
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Draw the structure for the final major organic product of the following reaction.
\par
}
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0 {
\intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
ffd8ffe000104a46494600010101006000600000ffe1002245786966000049492a00080000000100005
10400010000000000000000000000ffdb004300080606070605080707070909080a0c140d0c0b0b0c19
2ffdb0043010909090c0b0c180d0d1832211c2132323232323232323232323232323232323232323232
32323232323232323232323232323232323232323232323232323232ffc00011080046007c030122000
21101031101ffc4001f0000010501010101010100000000000000000102030405060708090a0bffc400
b5100002010303020403050504040000017d01020300041105122131410613516107227114328191a10
82342b1c11552d1f02433627282090a161718191a25262728292a3435363738393a434445464748494a
535455565758595a636465666768696a737475767778797a838485868788898a92939495969798999aa
60708090a0bffc400b51100020102040403040705040400010277000102031104052131061241510761
711322328108144291a1b1c109233352f0156272d10a162434e125f11718191a262728292a353637383
93a434445464748494a535455565758595a636465666768696a737475767778797a8283848586878889
0aad7d7f6ba6dab5cde4cb142a40c9e4927a00072493c00393daa9ea3ad2db5c8b0b280deea6ca185ba
36046a7a348dd117f327076824536c74565ba5d4754985e6a001d8db7115b83d444bdbd0b1cb1f5c700
02aff6ceb11b1be9b4675d2c8c08d096bb41ff003d1a31c107fb809618e849dabb769796d7f6b1dd5a4
f1cf048329246d907f1a9ab1aef45961ba9350d1a54b5bc73ba689c1f22e4ff00b6a3a37fb639e99dc0
62803668accd375a8af666b39e27b3d4635dd25a4c46ec7f790f474ff687d0e0f15a740051451400514
51400515cef8b6597cad26c52ea4b68aff504b69e589f63ecd8efb430e54b1455c8e7e6e39acdb8b64f
0d788f4db3d2e49d6dafedee44d6cf3bc8a86340cb2aee24a9cfca71c1de33c81401da515e6d6fac6b9
27837c2de758cb14524da62bdefdb0334a0c916490393bbb83ebcd7a4d0023bac68ceec155464b13800
5607f685eebe7668ee6db4f3c36a4ca09907a40a783ff5d186df40d9c88b54805ef8becec35166934d9
ad1a586dba46f346e37799fdff95d4853c7cac704818e97a0c0a00a9a769969a55b182d22d8acc5dd99
8b3c8c7ab331e598fa939ab7451400514514014b52d2ad7558563b946dd1b6f8a58d8ac9137f7918720
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8a28a0028a28a0028a28a0028a28a00ffd9}}
\cell
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
ffd8ffe000104a46494600010101006000600000ffe1002245786966000049492a00080000000100005
10400010000000000000000000000ffdb004300080606070605080707070909080a0c140d0c0b0b0c19
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21101031101ffc4001f0000010501010101010100000000000000000102030405060708090a0bffc400
b5100002010303020403050504040000017d01020300041105122131410613516107227114328191a10
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\cell
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
intermediate
\par
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
}
product
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
ffd8ffe000104a46494600010101006000600000ffe1002245786966000049492a00080000000100005
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\cell
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
final
\par
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
}
product
\cell
}
}
\intbl \row }}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
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15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f0 \b1 \fs22 \cf1 \i0
20.\u160\'3f
}
}
{\f0 \b1 \fs22 \cf1 \i0
Problem 11.35i
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Draw the structure of the products that would be formed when cyclopentanol reacts
with
}
{\f4 \b0 \fs18 \cf1 \i1
tert
}
}
-butylchlorodimethylsilane, followed by HF.
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
Product containing fluorine:
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
Product not containing fluorine:
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
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\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f0 \b1 \fs22 \cf1 \i0
21.\u160\'3f
}
}
{\f0 \b1 \fs22 \cf1 \i0
Problem 11.36
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Starting with isobutane, use the reagents (A - J) below to show how each of the
following could be synthesized.
\par
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0 {
\intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
A:
\cell
}
}
\intbl \intbl
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\cell
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
B:
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
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\cell
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
C:
\cell
}
}
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\cell
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
D:
\cell
}
}
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\cell
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
E:
\cell
}
}
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\cell
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
F:
\cell
}
}
\intbl \intbl
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G:
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H:
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I:
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J:
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\u160\'3f
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\u160\'3f
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Intermediate
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}
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\u160\'3f
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(b)
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}
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\u160\'3f
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44441ffd9}}
\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0 {
\intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
isobutane
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\i0 \pard{
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
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\
3f\u160\'3f\u160\'3f
\nestcell
}
}
}
}
}
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
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\nestcell
}
\intbl
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\cell
}
}
}
\intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
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\cell
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\i0 \pard{
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
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\
3f\u160\'3f\u160\'3f
\nestcell
}
}
}
}
}
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
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\nestcell
}
\intbl
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Intermediate
\cell
}
}
\intbl \row }
\intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\cell
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\i0 \pard{
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
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\
3f\u160\'3f\u160\'3f
\nestcell
}
}
}
}
}
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
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283742ffc40014010100000000000000000000000000000000ffc400141101000000000000000000000
\nestcell
}
\intbl
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
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\cell
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\i0 \pard{
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
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\
3f\u160\'3f\u160\'3f
\nestcell
}
}
}
}
}
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
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\nestcell
}
\intbl
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
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\cell
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Draw the structure of the Intermediate in (b).
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(c)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
}
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}
\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0 {
\intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
isobutane
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\i0 \pard{
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
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\
3f\u160\'3f\u160\'3f
\nestcell
}
}
}
}
}
{\intbl \itap2
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\nestcell
}
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}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\cell
}
}
}
\intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Intermediate
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\i0 \pard{
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
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\
3f\u160\'3f\u160\'3f
\nestcell
}
}
}
}
}
{\intbl \itap2
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\nestcell
}
\intbl
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
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\cell
}
}\f4 \li0 \b0 \chcbpat2 \ql \fs18 \ri0 \cf1 \i0 \intbl \row }
\intbl
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\cell
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\i0 \pard{
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
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\
3f\u160\'3f\u160\'3f
\nestcell
}
}
}
}
}
{\intbl \itap2
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\nestcell
}
\intbl
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
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\cell
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\i0 \pard{
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
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\
3f\u160\'3f\u160\'3f
\nestcell
}
}
}
}
}
{\intbl \itap2
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\nestcell
}
\intbl
}
}
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}
\cell
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Draw the structure of the Intermediate in (c).
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
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15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(d)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
}
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18c60318c60318c607fffd9}}
\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0 {
\intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
isobutane
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0 \f4 \li0 \b0 \chcbpat2 \fs18 \ri0 \cf1 \i0
\qc \pard{
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\nestcell
}
}
}
}
}
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
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283742ffc40014010100000000000000000000000000000000ffc400141101000000000000000000000
\nestcell
}
\intbl
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
\u160\'3f
\cell
}
}
}
}\f4 \li0 \strike0 \ul0 \b0 \sa0 \sb0 \fs18 \ri0 \cf1 \nosupersub \i0 \qc \intbl
\intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
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4141414141414141414141414141414141414141414141414141414141414141414ffc0001108003c00
4c03012200021101031101ffc4001d00010100010403000000000000000000000007060103050802040
9ffc4002b10000201040104000601050000000000000102030004050611071213210814223132411851
545597d4ffc40014010100000000000000000000000000000000ffc4001411010000000000000000000
\cell
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
\qc \pard{
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\nestcell
}
}
}
}
}
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
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02d100001030401040004060300000000000001020506030407080900111221131922590a14151698d7
283742ffc40014010100000000000000000000000000000000ffc400141101000000000000000000000
\nestcell
}
\intbl
}
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
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0301000010401030104090501000000000000020001030406050711121317214115183155669597d4e2
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\cell
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
\qc \pard{
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
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9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\nestcell
}
}
}
}
}
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
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\nestcell
}
\intbl
}
}
}\intbl \cell \row }
\intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
\cell
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
Intermediate 1
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
\qc \pard{
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
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\
3f\u160\'3f\u160\'3f
\nestcell
}
}
}
}
}
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
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\nestcell
}
\intbl
}
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
Intermediate 2
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
\qc \pard{
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
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\
3f\u160\'3f\u160\'3f
\nestcell
}
}
}
}
}
{\intbl \itap2
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
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283742ffc40014010100000000000000000000000000000000ffc400141101000000000000000000000
\nestcell
}
\intbl
}
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
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18c60318c60318c607fffd9}}
\cell
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Draw the structure of Intermediate 1 in (d).
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
Draw the structure of Intermediate 2 in (d).
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f0 \b1 \fs22 \cf1 \i0
22.\u160\'3f
}
}
{\f0 \b1 \fs22 \cf1 \i0
Problem 11.38
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Using the reagents (A - G) below, provide the reagents necessary for the following
syntheses. More than one step may be required.
\par
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0 {
\intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
A:
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
NaOC(CH
}
{\f4 \b0 \fs18 \cf1 \i0
3
}
}
)
}
{\f4 \b0 \fs18 \cf1 \i0
3,
}
}
(CH
}
{\f4 \b0 \fs18 \cf1 \i0
3
}
}
)
}
{\f4 \b0 \fs18 \cf1 \i0
3
}
}
COH
\cell
}
}
}\f4 \sub \ul0 \b0 \chcbpat2 \ri0 \qc \i0 \li0 \strike0 \sa0 \sb0 \fs18 \cf1
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
B:
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
CH
}
{\f4 \b0 \fs18 \cf1 \i0
3
}
}
C(O)OOH
\cell
}
}
\nosupersub \intbl \row }
\clbrdrl \trql \cellx2687
\trql \cellx5374
\trql \cellx8061
\clbrdrr \trql \cellx10748
\intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
C:
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
NaOH, H
}
{\f4 \b0 \fs18 \cf1 \i0
2
}
}
O
\cell
}
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
D:
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
PBr
}
{\f4 \b0 \fs18 \cf1 \i0
3
\cell
}
}
}
\nosupersub \intbl \row }
\intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
E:
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
Br
}
{\f4 \b0 \fs18 \cf1 \i0
2
}
}
, H
}
{\f4 \b0 \fs18 \cf1 \i0
2
}
}
O
\cell
}
}
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
F:
\cell
}
}
\intbl \intbl
{\li0 \f4 \b0 \ri0 \fs18 \cf1 \qc \i0
H
}
{\f4 \b0 \fs18 \cf1 \i0
2
}
}
O, H
}
{\f4 \b0 \fs18 \cf1 \i0
2
}
}
SO
}
{\f4 \b0 \fs18 \cf1 \i0
4
}
}
cat.
\cell
}
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(a)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
}
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fd9}}
\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
The reagents needed for the synthesis are:
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
1.\u160\'3f
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\par
}
}
}
}
; 2.\u160\'3f
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\par
}
}
}
}
; 3.\u160\'3f
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\par
}
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(b)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
}
ffd8ffe000104a46494600010100000100010000ffdb004300030202030202030303030403030405080
141812141514ffdb00430103040405040509050509140d0b0d141414141414141414141414141414141
4141414141414141414141414141414141414141414141414141414141414141414ffc0001108003c00
c203012200021101031101ffc4001d00010003000300030000000000000000000005060702040801030
9ffc4003a100001030402010202030f0501000000000100020304050611071221133122410814171523
2432333738576176818492b3d434424351b471ffc400150101010000000000000000000000000000000
1ffc40014110100000000000000000000000000000000ffda000c03010002110311003f00fd5344441d
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d2d3f0bfe21f17467b20de511101111011475ff22b5e2b699ee779b8535aedd00ed2d4d5ca238dbffd2
7e7fb3e6b2fc8b2be47e42b3543f8fececc72806bd3ba6460d3d656336d2efab53ba37fa3b6977592a5
9f8cd1b84b487a0be661c8764c23ead15c2a1f2dc6ac91476ba289d3d6551f6fbdc2cdb88048dbb41ad
dedc5a3ca82b65bf2fce2adb5591321c6b1c7c6f61c6e3f4ea6a6ad8f8dcc22ae6f2c60f8b7e9c3bd16
8fbeb86daa33882af10a2b8565be9a86bacf9bcacf52e54f923bbddaa003f8e662e709e205da0e89ce8
9bbeadebaea35541e6ec7309e5de22a2b7f1be219561572b2c74d39b2d464ada86dd68a86231b437d18
be0a91099a2677ed1f8733b6f6b59e1ae2da6e1fc169ec10d7cf77ab74f3575c2e952d0d96bab2791d2
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e45a286df4a34d66536d6b8dae4f1ef383b7521f1ff00217463607aa49d2d1a09e3aa8239a19192c323
43d9231c1cd7348d8208f70420fb1111011110111101756dd6ba3b3d37d5a82920a2a7ece7fa54d1363
6767125c74001b24924fcc95da4404444059ddcf93eb2fb70aab46056c66435f4d3ba9aaee9532186d7
43231fd246be50099a4610f06288121cdeaf745bd8d117c0007b784144c7b8aa18aeb4f7eca6e1265f9
3407bc35757188e9a89de7fd253025b0f82477dba423c3a472be222081cc706b1e7b6c1437ba16d5c6c
77786663dd14f4cfd6bd4866610f89e37e1ec7070f91551f5736e3477df44fc858c83f958dac65e68db
fb5a3ab2ada3cf96f497407c32b8ed6988831ba3ccacb9c73fe0970b1dc22afa718a6451c819b6c90c8
2b2cbb8e461d3a378f9b1c0387cc2d9141b307c7e2cc5d9632cd451e4cea336f7dd990b5b50fa72f6bf
d273c79737b31a403bd6bc6b654e2022220ab66771cae39696df8b5ae9249ea5af325e2e72fe094206b
5b898e124cf3bf0c1d1ba69dc8df00f4f19e2da1b4ddd97dbc56546539380436ed730d269c1f7653c4d
019037e5f000e7003bb9e7cabaa2022220e2f63646398f687b1c345ae1b047fd159bd4715d761f3c95d
c73718ac3d8b9f263958d3259ea1c4827ab07c54ae3a3f143a6ede5ce8e43a5a52208ac66e771bb59a1
a8bada24b15c097325a27cec9c34b5c4766bd874e63b5d9a486bb446dad3b0255110111101111011110
1111011110111101111011110111107fffd9}}
\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
1.\u160\'3f
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\par
}
}
}
}
; 2.\u160\'3f
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\par
}
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(c)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
}
ffd8ffe000104a46494600010100000100010000ffdb004300030202030202030303030403030405080
141812141514ffdb00430103040405040509050509140d0b0d141414141414141414141414141414141
4141414141414141414141414141414141414141414141414141414141414141414ffc0001108003c00
fe03012200021101031101ffc4001d00010002020301010000000000000000000006070405020308010
9ffc4003510000103040103010603080301000000000102030400050611120713213114151622415123
326108171833425796d5718291b1ffc4001501010100000000000000000000000000000001ffc400141
10100000000000000000000000000000000ffda000c03010002110311003f00fd53a52940a5559905c2
6757320978b59df761e256f74b37fbc30b28724ba92926df1d43ce88d879d1f947e1a7e75294d660e9b
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a51005408e5597752165ac4e1af16c7d5e15925ea31f697c78f3121af44023969d7f8804021a7527741
28cd7a8d8ff004fa3b0bbd4e5372249298b022b0e4a992d406ca598ed254e3a40f24212743c9d0acdc5
b2eb366d694dcec5728f748456a6cb91d7be0e24e96dac7aa169208521402924104022b5b8774d6c985
48933a2b4ecebdcc484ccbddc5c32274a009212b755e4201528a5b4f1427678a522b1327e95dbef5785
5fad52a4e2f9494a506f16be295be94fa22436a050fa3e9a7124a413c0a09dd04d69559b5d4bbb609a8
dd4782c428c9d25395dad0b36b73c7953e9254b8677bfe6153636077493aade7533aa367e96604fe5d7
24499d6a69d88d6adc10e2d7ed121a61b5279292929e4f2493bfcbb23674084c294a50294a50294a502
94a50294a502955fde7ab0dc9bac9b1e1b6e565f7e8eb2d48ec3bdb8101c03f2ca95a2942bd36da02dd
f20f0d1dd6ba4f4f738700bf7c72eab2a6495b36f6dbed59148fac65b1f32c85687e31517127ca7492a
6d4168d2a29837502366225c27e32ecf91dbb8a6e56592a05e8aa56f8a811e16d2f8928713e1401f421
4912ba056ab29c9adf86e3f3af57578b1021b7cdc525056b57901294246ca96a51094a402544800126b
6b5565a41eb066a8bd3a85fc198e4a522d4dabf25d2723e55ccd7f534c9e4db7bf05616e6884b4aa0b4
1973bcd21ce2a4724857158d286fe847d0d73a52814a528155ae61925c335c8e460b8aca7622d84a4e4
17d63c7bb595a494b0cabd0cb706881e7b483dc568a9a0bd9f59f22bb62bd3ab9dceceb4c77d92d07e7
29b0efb04653894bf28367c385a6cadce27d787d7d0eeb09c52d38663716d966493087278beb73b8e49
71c515ade5aff00ad6b528a8abea4d066e3f60b7e2b658768b4c46e0dba1b61a61868692848ff00e93e
a49f24924f935b0a52838b8da1e6d4db890b42814a92a1b041f504555794f4ca060766bc64586dca4e1
4fc48cecc76242d2ed8f14216b3dc86adb69d924a96d06d6ad0daceaad6a80f5f1a7a5f45338851de5c
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29692b55da1f22847a201237a4803649d6c927d195817cb05b326b6b96ebc5ba25dadee290b5c49cc25
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24a509c821c6beb9359b4a7e5e2fa5f54463b6e29049ec6dd2bd0212decad5ea1a08f66b9b42c1adb1a
4ca625cd91324261c281019eebf2df5254a4b681e003c50b254a294809249006ea2630fcaba900b999c
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0a2406d0a1e52fbe52a4208f284a5c5ec14a02a7f6ab5c3b1db225badf19a85022328623c661010db4d
a404a50948f00000003f4aa5f03ba5cba196d94cf50a0209b84954fb8e736edbb164c85a520ae5a35ce
2f1090da49e6ca5b69b1dc4f848bb62cb627466a4c679b911dd485b6eb4a0a42d27d0823c107ef41db4
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5e5fb61568343ee632c8688f27816144ed7565541baad8c4fbadae0df2c08e594e3cf99f6f6f9f01287
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dba52940a52940a52940a52940a52940a52940a52941acc9ec11b2bc6aed649a90b877288f4379246c1
43882850ffc51ad2f492fb2f25e98e2f71b82035737adec89ad8572edc94a425e4efeba712b1bfd2a5b
55ef48822d6e66b8f21b5b49b4e4529480b24f24cb089fb4ecfe5e52d6903d0702078141615294a0557
17e57c6dd5bb4d8d3c956bc61a4dee78d1e2e4b739b70da3e34ae203ef11bda5498e75f303537c86ff0
315b05caf574928876db746725ca90e1012db484952d449fa0009a8bf486c736dd8b3975bc3063e4190
c95de2e2d2c00a65c702436c1d1236cb28659d83e7b5bfad04dc80468f9155dcbe953d8d4a76e3d3fb8
378c497165c7ed0eb65db4cb255b5153008ecad5e7f11929f276a4b9e9562d28284bfe6fd41ea3f5464
f4f314b9c0c1dcb15a225c325bdb6c26e4eb322505f6a2c54ba94a0801a5a8bae23c809f906cd6a2e5d
48cffa4391dcb0acb6ff001b2755cf1ab95df1bc99b80dc49224436925e664329db4a203885a569001f
20a6a41996199af4fbac774ea3e0b658d9744c82db1e05f71e726a21c953918b9ecf223babfc3278bab
4290b29fa10af5a8fdcba6f9ff0057b23b966b96d823630ab663572b46378cb73db9724c898d243cf48
793a692486d084a12481e49551593fbfb57f069f187c5d6cf8efe01f7b77fbb1fbbef1f7777797675c7
9777cf0e3adf8e3af157474f2eb2afb80633729cef7e6ccb64690fbbc4279b8b692a51d0000d927c01a
af3c7f0878c7f091ee2fdd662bfbcdf81fd8bbbeeb85ed5ef6f60e1cbda75aee77fcf779eb7f372fad7
a1fa796a9562c0319b6ce6bb1361db23477dae415c1c43494a86c120e883e41d5048694a5115b46e99e
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12c31d75db0e3369b43ef2b9bafc384db6ebaad6b92d607251d0036493e2a4b4a50294a50294a50294a
50294a50294a50294a50294a502a2b9174c31bca2e4e5c26c279bb83884b6b97066bf0dd5a53be214b6
568275c8fa9fb7d854aa941018bd1e856c60356dc9b2e8413be2a7720933543cefd6529ddf9fbefede9
e2b8c7e9de536f71c547ea7dfe5a54ae4966e906dcea1b1e7e505b8cd288fd54a27c0f27ceec0a5055f
78e9d66f94498106fb9859e762c894cc99b063d85c8f2e50695dc4b7dff006b52036a5a1be69ed1e49e
69d80aab4294a05294a05294a05294a0ffd9}}
\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
1.\u160\'3f
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\par
}
}
}
}
; 2.\u160\'3f
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\par
}
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(d)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
}
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\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
The reagent needed for the synthesis is:
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\par
}
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(e)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
}
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164ec1b3a64ad7346f6003dd4c5105667912f7c7ad31720d0c66d718fad9688dc68c346bcd550925f4b
ea76edbe20012e7b3d158b455b4f72a386ae9278aaa967609229e1787b24691b0e6b876208f98598804
68f70abaabe27931cad9ae9c7f71662b572c8e96a2d4f88cb69ac7b9c5cf73e9c11e148e25c4cb09612
5db78935a413fadada7b6d1cd57573c54b4b030c92cf33c3191b40d9739c7b0007ccaae8721def90c08
f8fe8a26da9e3be597789c28cb4efcd4b082d7d49f4d3b6c88820b5eff00459a9389e4c8eb61ba7205c
599555c52365a7b5322315a68ded70731cca724f8b23486912cc5e416ed823de958a000343b0410ec43
8b2d58bdc5d79aa9eab22ca246164b7ebbbc4b53d2400e644000c8233d2371c2d63491b209249992220
22220222202222022220222202222022220222202222022220222202222022220222202222022220222
20ffd9}}
\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
The reagent needed for the synthesis is:\u160\'3f
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\par
}
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(f)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
}
ffd8ffe000104a46494600010100000100010000ffdb004300030202030202030303030403030405080
141812141514ffdb00430103040405040509050509140d0b0d141414141414141414141414141414141
4141414141414141414141414141414141414141414141414141414141414141414ffc0001108004e00
f403012200021101031101ffc4001d00010100030101010101000000000000000006050708040301020
9ffc400421000010304020101050307080b0100000001020304000506110712211308142231413576b4
15162332333751182456737591b2d209263643445361627172b382ffc40015010101000000000000000
00000000000000001ffc4001511010100000000000000000000000000000011ffda000c030100021103
11003f00ff0054e94a50294a50294a50294a5029515cd5c9b1786b8a728cd65b065b56684b9298e15d7
d673f55b46fe9d965237f4dd6b35e37ed056bb044c9d199d9efb9080dbf2f083696a3db9692a05c8ec4
a2a0f21612484bae294925236800f80e81a56acc1f36bd5e79ff009331c9928aacb67b5d8e4c186a69b
058724099eb12b48ecaede8b7e0a881d7c6b677b4e814a52814a52814a52814a52814af8cc98c5be2bd
2a53edc68cca0b8e3cf2c2108481b2544f8007f135ae4726df338581c796562e36c076ac8ef4e2e35bd
e1a275182525c91b3a1ea0096b4a2a4ad653d086cca54263dcad1645de35832582ee25933ff000b3067
2c29898a1bdfbac81f03ff00227a8d38079521357740a52940ad087dae22c99d92b76be2ee44bf40c7e
e92ed132e76ab6c57982f4670a1e2d8f790e2c0236348ec47d37e2b66c3e5ac42e3c8b2b038b9042919
6c589efafdada73b3ad35d80dab5e01f893f0fcf441d68d727f174acb1a87cc3f91b99715e3f849cef2
3fe6d77b3b721f615ef4bdbbeaae5b600f911b6c81afad15d8784e6768e44c46d193582589d66bac644
a8af8494f74286c6d27441fa107c8208359bae15e09c4f1fe4eca784edf32cd22db6089c79365b56a6e
6ba1a90b8f728cd34f2940a54eb6b2a2fa42c68f66d453b48d775510a52940af9c890d4461c79f710cb
2da4a96e38a094a40f9924fc854fe75973d895be19876d55dae9719420c1861e4b2871e285ac7770efa
2025b5124051f1e124e854db1c55272d92d4fe43b83791290a0e33608e82dda23281da4968ecc858f1f
1bc48da429286cd07c55c9b76e414298e3686c4c84b4ff00b5d7442bf25a763c2a3a1252b99f43f0143
441fdaec6abfb5702d8ee7fcfafd3eeb7cc981ecde44e4c5312e21fe114b5d531d1f4286c00b1e17df6
77b2929090000001e001f4afda0d649be663c64df4c85a7f38c75b1f6e5b6301728e803c99315b003df
2f2b8e90493fb10076abbc7b24b565b6966e766b847b9c077611222b8169241d1048f9107c107c82083
a3592a85c8f8a224ebcbb9063d3dfc4b2773f6970b7805a97f2f12a39fd1be3e103b101c48d842d1b34
17558ac9729b461d6a5dcaf7718f6b8285047ad2561214b2749427eaa528f8091b24f8009ad76d677c8
72af1230f4e3b6963276233729dbeaa595da830e29c421d4b3b0fa9cecd2b6c1ea91ff003cfccd0e31c
5506d3774dfaf73a4e579400a09badcc2751812494466520371d3e75f00eea00775ac8dd04ae73619be
d29c6d96e272ec7271cc5ef36d5c78972b9edb98e3e48536efba6b686d24057e914959234509f9d4d4b
baf3f65f8b3388398a40c3af4e86a34fce63de9a9315b6c11eabf11809f58baa483d50e25094958da94
079e87a506abc1306bcd8b9f392f21971942c976b558e2c198b790b53ee471303c0a41ec0a7d56fca80
07b78de8eb6a52940a52940a52940a52940a81bef2c30abacbb0e2501597e49195e9488f15d0dc482be
a1404b93a2968e8a4f4016ee94086c8f3595e5590ec5e2fcc1f61c5b2f376698b438da8a54850616410
47c883f5af7e1b64b7e3b8adaadf6a831adb0198e80dc688d25a6d03a83e129000f341271b8a1dc9a53
371e41b837944969c4bcc5a1b68b56988b4abb20a5824facb4900871e2a20a429096fe55b1400068781
5fb4a0c6e418e5ab2cb4bf6bbd5ba35d6dcf8d39165b41c6d5fc3c1fa83e41f9835069c7330e33daf1c
96fe698ea367f205de4eee11d3a1e234c70fe9078fd9c82492a3fa6480135b3a941238ff002ae33905b
ee3245c536c72d682e5ca1dd47ba488091bda9e6dcd1427c1d2ff0051406d2a23cd726f2cfb4df27fb4
2bf2711f66dc7a6bf6a52d4c4de4094dfbbc4001eaa119c7349f077b58dabe7d53f2557457386098e66
777e3f45fac56ebca0df92ca933a321e0a6fdda439d0f60769eedb6aea7c12849d7815b4a3c66a230db
0c3486196d21286db484a5207c8003e4283897d957fd1c8ff0c6756ee42cb7389774cbe32d6f7bbda49
4472b7124381d75c056f857656fc237f5dd7504df67ee2eb95e5fbbcbe36c4255d5f90a94f4f7ac5156
fb8f295d94e29c2df62b2a254544ec9f357d4a2d63d38fdad17662ea9b6c34dcd88ca84d4d0c23d66e3
a949529a4af5d820a9082520e894a4ebc0ac852944294a50437257db5c7df7893f829757350dc95f6d7
1f7de24fe0a5d5cd0294a50294a504342fdf85e7eeec1fc4cbab9a8685fbf0bcfddd83f899757340a52
940af05fafd0318b449ba5d25221c08c90a75f737d500903675ff00522bdf4a0d6ffca338dbfa5b07fb
97fe5a7f28ce36fe96c1fee5ff0096b6452835bff28ce36fe96c1fee5ff96a2733f6d5e3bc0f24b447b
9dcda731fb9ad31917a86a53beed24f6210f33d429282078711dc6c28282068ab7f54e5d38f71fbee57
6fc8ee76e45c6eb6d47580b96a2e370c9df671a6c9ea87083a2e01db5a1bd78a0a3a5294125cbbfba7c
d7fb126ff00f05d50597ec781fd437fe1153fcbbfba7cd7fb126fff0005d50597ec781fd437fe1141ed
a52940a529410dc95f6d71f7de24fe0a5d5cd437257db5c7df7893f829757340a52940a52940a529410
dc95f6d71f7de24fe0a5d5cd61b2bc42d19bda156cbcc412e295a5d414ad4db8d389fd571b71042db58
fa2d04287d0d46ff00aebc6caff88e41c6c1ff00b1178889dfff0096e5240ffd1cd27fdea8d06cba560
f10cdec99ddb153ac7706e6b2dacb4f23aa9b7a3b83e6dbad2805b4b1b1b42c050fe159ca052bc579bd
5bf1db5c9b95d6747b6dbe320b8fca96ea5a69a48f9952944003ff0035afff003c729e473e9e190ff20
5895aed93dee3282dd4efcfba4457552b637a75dea804a54943c9f1419485fbf0bcfddd83f899757352
f85f1e5b309f7990cbb2ae7789a9409d79b9bdeb4b97d77d7bab402520a95d5b404a13d8f548dd54502
94a50294a50294a50294a50294a5061f32b0ab29c42f96543c23aee305f861e527b04171b523b11f5d6
f7aa8db27297e6cbf02c19ddbff352e4beb1a2dc0b9eadae7afc2521a93a010b51234d3c10b27610161
2555b2abcd71b6c4bc4091067c5667429082d3d1a4b61c6dd411a29524820823e8683d34ad669c0720e
3c597b05b8099684ebb6277a7d4a8e81b24fba48214e307ce836aeed0ea9094b6366b3988f27dab299c
e5a9f6e458724611ddfb15d921a9484f8dad1a252f363607a8d2968df8defc5058563efd7fb662f6993
74bc5c235aedb193dde9731d4b4d363f89528802a26572c3992cd7ed7c7f6f46512d970b326ecb70b76
986b0aeab4adf00face248502d3214414f5596f7baf4d8b8a5a55d235f72db82b2ec898507187a4b5e9
c382bd6b71636ca5a3e4fc64addd120ac8f141894dd2efca99363b36dd63916cc4ecf38dc3f2a5d82a3
c8b82c30eb494c78c4770d9f5492e3bd0fc03aa1695771576fe41b6bb2150ee5dac9706fe1723ce2100
ad31d0fba1b5feab896d2e00a5a7690411bd8355153d9860765ce212a3dd61b6f7647a25d0901c5325d
6dc5b055f3f49c2cb6168040584e8d050254140104107c823eb5fb5a219b2721e259359ed4cdd9f9eab
83ed36f5cbd1eec12a70cab8cb5b6a5a8348e886e2c76b64b65c27e24826bcd68e55e53e5e174be71a5
b7128b874399220c29192ae4adfbcad8714d3ab6fd12131daf510a4a54a0e13d49291e05074052b9ef1
bf69d9998e4dc516f856962d8ac8aef79b26436f984bb22dd2e04579c5b4dad2a093fa5687c4527b214
3c249f17599f255cf1de71e35c323311176bc961dde44c79d428bcdaa2a23a9b0d90a09009795db693b
d0d6bcec3655294a05294a08dcbb8b6d394dc91798eecac7f276901b66fd68586a504807487360a1f6c
7627d3792b46fc80080460ce41c9f6529b33b8bdbf249ce6d31f228b3130e00035b5ca65654f34af274
9643c15afd66f7e367528202cdc54997738d7bccee272ebe30a0ec74bad06adf057a1e6346d90923e8e
3856e7923bebc55fd2940a52940a52940a52940a52940a52940a52940a52940ac1e5983e3d9e40442c8
acb06f5150aee86a73097424eb448d8f1b0483fc4120f8359ca507c21428f6d86cc488c35162b080db4
c32808436903412948f0001f415f7a52814a52815cc3c5f93dfbd99314778eaf18065b93336b9728d86
eb8d5bbdf58b84475f71d690e292a018751dfa2bd5ea9f8410a3bae9ea507130f670bd5ef26e2b4e6b6
49eefe70e5d9164d91336992fa1bb519309c31d95ca8e5051d7a30df60a485ab69da81f3789f67cb471
97b4ff0014dd710b2deff259b75f11749b26e13ae2cb0a2dc60c052df71c4b2544b9a00a7bf53f3ea35
d3b4a294a5288ffd9}}
\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
1.\u160\'3f
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\par
}
}
}
}
; 2.\u160\'3f
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
\
3f\u160\'3f\u160\'3f
\par
}
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f0 \b1 \fs22 \cf1 \i0
23.\u160\'3f
}
}
{\f0 \b1 \fs22 \cf1 \i0
Problem 11.39
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Predict the major product from each of the following reactions.
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(a)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
ffd8ffe000104a46494600010100000100010000ffdb004300030202030202030303030403030405080
141812141514ffdb00430103040405040509050509140d0b0d141414141414141414141414141414141
4141414141414141414141414141414141414141414141414141414141414141414ffc0001108003500
b603012200021101031101ffc4001b00010002030101000000000000000000000006070405080903ffc
40033100001030401030205020407000000000001020304000506111207132108141516223141173218
515561093342529296d4ffc4001501010100000000000000000000000000000001ffc40015110101000
00000000000000000000000000001ffda000c03010002110311003f00f54e94ad365798d9708b67bfbe
5c5ab7c62a0db7cf6a5bcb3f66db4241538b3f8420151fc0341b9a88661d5ac4b039ccc2bdde111a638
8ee98ecb2e487196b7a2f3a96d2a2d320fddd738a07e542a0198751af7736a3899264f4f6cf317c2245
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1687127ec52a1e08fee2bef55dcee94aec339ebae05704e2b3dd5971fb696bbb6a98a24951723823b6b
5124975a28513e55cf5aafa597ab0dc7b9c6b1e656e561f7f90b0cc7121d0e409ebd7da2cad04ac9f3a
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2e3852da77f528504b2a14e759f0a67233635e41184e0efb7539c57ed92f93a0c2a471ed078fe1a2be6
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6ae76b8feeae56bbe20477e1b406d4e28eca16d0d11dd6d4b6c9074a3a34133a5511fc61e2dec3e39f2
be69f2471ee7ce5f035fc33b7cb5dddf2ef76b5f5773b5c35e77561dabab562bdf523e4c825e9534d82
3e48dcf6782a1bb11e79c69be0b0ad9512d957ede3c482147ed4134a544ec1d4ab6645d44cb30c8cc4b
45d31a620c898f3a84865c4ca4baa6c36428a89019572da46b635bf3a9650294a50294a50294a50294a
5061de199d22d52dab64a6215c56d2931e4c960bedb4bd7d2a5361482a00fe390dff3aa46c18664177c
81f9d67625c69df5c7919ee60c876e2b4ec0522df0b494476ce8fd4a4b69da52a2d3c0f2abea94116c3
ba6d65c29e93322b6f4ebccb004cbcdc5d2fcd93a2480b74f909049d369e284ef494a478a94d2940ac0
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0c2b1eccee16db0650a9892ccb4266ca801867ba44490e92a4857db8ba1d091fb3800055af87e0563c1
633edda21069e92a0e4b98f2d4f4a96b035cde7964adc56bc6d44e8781a1e2b9d7d44e42607ad3f4c71
439a485df4a90093b2ec44b49247fc803f8d9aeaaa05294a05549ead315bc66be9bba8766c7d97245e6
55a1d4b0c3236e3c0694b6d23f256949481f9240ab6e9414cff12bd25fd1ff0098fe64b47cbfec387c2
fbe8f71fb38fb4f6ffbfbbfe8edf1e5bf1aae66e82f4e3a9769ea3e1361b6e531f0ac8a0f49adbef85d
2cbf113c157298a432505e6b82900a41f27ec46abb63f4bb0cf99fe64f946c5f317f57f86b3eefefbff
3b8f3fbf9fbd6e1360b626fabbd8b7441795c64c355c4309f70a612a2b4b45cd72280a529413bd02a27
5b34573bfa72b4e4765f52bd738d956431b27bb8818e2953e25b4406ca4b7378a435dc735a1f9e477fd
aba5eb022d82d906ef3eeb1add123dd27a5a44c9ad3094bd252d8506c38b0392c202d5c41275c8eb5b3
59f44579d6fbd65363c560b98b332d4e3d70699b84ab7454cb9912194acade8ec2810eb8141b4f1215a
0a52b8ab8f1350db7ad193ce365c46c997b776bc5fafc9b5b177bf589c8172b530884f4a7ccb84a6d94
a9d3ed96969410842bb9bd1e042af8cfba776eea144b7a65499b6d9f6c93ef2dd74b63a1a950deedadb
2b6d44292768716929525492144106a22bf4df8d4e832cddae37abd5fe4488b2ce4d2a5a5bb934f470b
0c29a71943686f8075e1c5080921e702810b502100cf7ab9977a6b91748b90de4f5161af15ba5fedd2a
5c5661cb6e4422cf365eec212da9a58928d28212a4f6d5be7bd898a2d3d4ec3988978b97506db7f6df4
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294a50294a50294a50294a50294a50294a50294a50294a50294a50294a50294a50294a50294a507ffd9
}}
\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
Draw the product:
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(b)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
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2e497523e816f2dc57fbb2518c06318c06318c06318c06318c06318c06318c06318c0fffd9}}
\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
Draw the product:
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(c)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
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4141414141414141414141414141414141414141414141414141414141414141414ffc0001108002700
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000000000000000000000000000ffda000c03010002110311003f00fea9d294a052b5b906476ac4ed2f
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\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
Draw the organic product:
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
Draw the inorganic product:
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(d)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
ffd8ffe000104a46494600010100000100010000ffdb004300030202030202030303030403030405080
141812141514ffdb00430103040405040509050509140d0b0d141414141414141414141414141414141
4141414141414141414141414141414141414141414141414141414141414141414ffc0001108005700
b203012200021101031101ffc4001d00010002020301010000000000000000000006070508010304020
9ffc4003910000103040102040403050803000000000100020304050611120721131422310815415117
326123335795d409161824374284b3627191ffc4001501010100000000000000000000000000000001f
fc4001511010100000000000000000000000000000031ffda000c03010002110311003f00fd3fc9727b
5e1f679aeb79ac6505b612d12d54a0f8710240e4f201e2d1beee3a00772401b5efa5aa86ba9a2a8a69a
3a8a795a1f1cb138398f691b0411d8823eabb1cd0e0410083d883f555cd674aaa719ab92e3d3db9478c
cef79967b2cf1196d156e2ee4f26104182477abf69096f77727b25d69058e8a0360eacd3baeb4b61cae
81f87e4d50ef0e0a4ac903e96b9fa27549520064dd9ae770f4ca00dba36853e40444404444044440444
40444404444044440444404444044440444418ebfe3d6bcaed1536abcdbe9aeb6da96f09a92b226cb14
83f5691a2a0b68b65c7a759bd92c7497baab9e33748ea045437526a27a17c4c6b9a22a9279ba3d6c719
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1110111101111014272bff52b05ff009fff0048536553e7dd45c66cbd55c4a9abaf9454d2d0f98159ce
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0a1f62eb061992dfdf65b66454559700e7b18c8dc784ef612246c3211c25730821ed8cb8b0f676904c5
1110111101111016bbf577af776c33adcfc3d99bf4ff0004b4c58f525ddb5599c4f3255cb2d4d544f8e
2779c81a035b030fb38edc7f40b62141dbd2fa77f582e59d5454c7522b2c5496516f92981f0fc1a8a99
bc5f10bbbf2f31c78f11ae1bd9de805097af8b1c80c98089ef78574da9720b1d7dce5b865b04d3d3cd2
415714110a72da983d1331e676f2d9e1aedeeac7e9e7c4ac1965b70482a6c370aabf653473d7c2cb346
d9a94534354ca775517bdede11384b1ca03bd41aee3ddfa69ccf50ba5593df7a9966cdb13cb6dd8edc6
82d15566921b9d91f718e58a69a098b871a984b5c1d4ed1f5ec4a8fe3bf0eeee9d55bf20b75f2bee373
86cb7d8248a9608a09aa2aee159156be580b898e1e32445ac639ae68e6dd93c4f22af34549fc363f22a
4872ea5bb555f2e1608eb23a8b4d7645495949511b5d1ea6a62cad7be7788dcc0f3317963ccce118631
81a2ea63db231af6383d8e1b0e69d823ee88fa4444051fcc33db1e0b4d04977ad114d52e31d251c2c74
d5556f037c218580be476bbe9a0e8773a1dd7ab29a2bc5c6cb2d358ae7059ae32398056d45279911339
0e65ace4d05fc79069712d0e2096b802d389c3ba6767c36a66b847e3dd6ff52c0cabbedd24f1eb6a003
be25fa018cd92447186c6ddfa5a1047dd6ecd3a9a1df3296a301c6a41af2147334ddea9840fde4ec25b
4a3dc16c45cfee089587b29858307c7f16b03ec96ab3d251daa4e665a56440b6673c9323a4decc8e792
4b9ced97124924959c4415a3ba7178c07f6fd3cad8a0a06f77629747b8dbdc003a6d3c8039f487dbb34
3e31aed10276b2f8af552d97fbbfc86e10546359535ae79b25d4064d2b5bae5240e04b2a231c9bb7c4e
771e403b893a53451bea059b18bc62f5672f8689d65a46f9a96a2b9c236d2f0ee266c9b062737dc3da4
16fb82104914372cea95b31cb98b2d153d4e4993bda1ecb1da1ad9276b4ef8be671219046747d72b9a0
eb4367b2a43a5f96e4fd4cb55dee36fcb2eb45d17a693c3a0c86ba38d979ad8d8e778d20a87901946d0
00133d9e39d38f31ae4b60b0ac5f1fc56c50c18dd253d3dbe702a3c581dccd4970df8af9092e95ceec4
bdc493ee4941111d39be7504f8dd44af85d6d7776e256791e283440f4d54c435f57df7e92238883a31b
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7e559af4cb46d134f9f634cf7b5dc2a036ed4ad00fee6a5e436a47e5019396bfb9266768354971eea6e
379259ae373a7b932961b6721728ae0d34b35bc86f270a88e40d745a1df6e0011dc12082a52b5ffe35d
910e92dadd706b462e728b30c94b87a0dac5647e3789ff87e5e5bedaded04a31af8abe9565d9052d9ad
99853c95b59208a8dd3d34f4f0563cfb3609e48db1cc4fda37394eacb9cd9322c9322b05beb7cc5db1e
96086e74fe13dbe5df342d9a31c9cd0d76e3735de9275bd1d1ecaadf8bffeed7f857cebe67e53c97c9e
4f956b8ebcef0ff25e0ebfdfe2f87c78f7fb2a8ba4953d61a7eb4f5786376dc52beb48c7be6c726b855
534adaaf92d373e021824046f96f7a3bfba2b6bf16ce6c99acd7d86cd5be724b1dca4b45c0784f8fc0a
a6318f747ea68e5a6cac3c9bb6fabdfb1d6796bafc1a3ef5243d657645150417c3d42ae3571dae57cb4
cd7f93a2d88dcf6b5ce6fea5a0fe8b6291185cbec771c86c92515af22aec5eb1ce6b9b72b7434f2ccc0
0ecb43678e48f47d8eda4fdb4a05f8459cff001c72ff00e5564fe815ae882a8fc22ce7f8e397ff002ab
27f409f8459cff1c72ffe5564fe815ae882a693a479c88dc7f1bf309340fa05aac7b77e9de834b09f0c
3d13cc3a430645264d9954de692eb56ea8a1b039917816a61713a63a38e36073868b99146c8da77c41d
971bd110111101111011175cee919048e8982594349630bb8871d761bfa7fed047ba8dd48c6fa4d8857
e4f95dd60b3d9a89bca4a898f771fa318d1ddef3ec1ad0493ec168ce2f7bcb3fb4afa872beb22abc5fe
1fb1eac065b7b242c96f93348732395c3b1ff006b9cd0751820025c43c53f90e17d6af8f1f89fadc4f3
8a4aac3ec98dcfbaea06b4ba9ad101d6b813da69a51f95e77c812e1a63743f52f00c0ac5d30c3ed78be
35411db2cb6d84414f4f1ece80f77389eee713b25c7b92493ee8b195a1b4d15b6d705b692921a7b7c10
b69e2a58d81b13230de2181bec1a00d6becabbcbaf557d20ad9af4e73eaf13a890c9571c8f73df492b9
cf73ded24be499f238c10434d1340e475f51ab3d75d440ca985d148096bbec7447d883f423dc1fa223a
a82be1b8d3896270d83c5f1920ba27e812c7004e9c37dc2f4ad75ae8af1d12cae828edfe2cf6a9dc61b
75ba9dfc8d587485fe5a9e032174f59239865a8ada8706c6d7170ece908d81b6cb533dba965ada76525
63e263a7a78e5f15b14840e4d0fd0e401d8e5a1bd6f4107a579ee36ea5bbd05450d753455945531ba29
a9e7607c72b1c34e6b9a7b1041d1057a11054f8d7c2a74ab11c8296f36cc3e9e3ada3904b46d9ea67a8
828de3d9d041248e8e123ef1b5aa7565c1ac98ee49915fedf45e5eed90cb04d73a8f15eef30f8616c31
9e2e716b751b5adf481bd6cecf759e44181c5b06b261535f66b35179392f97292ef703e2be4f1ea9ec6
31d27a9c78edb130716e9be9f6ee779e4440444404444044440444404444044441d6d82264cf95b1b1b
2c8007bc3407380f6d9faeb67ff00abb1110111107c9634bc38b4170d8075dc6fdd7d22202222022220
2222022220222202222022220fffd9}}
\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
Draw the product:
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(e)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
ffd8ffe000104a46494600010100000100010000ffdb004300030202030202030303030403030405080
141812141514ffdb00430103040405040509050509140d0b0d141414141414141414141414141414141
4141414141414141414141414141414141414141414141414141414141414141414ffc0001108004c00
d903012200021101031101ffc4001d00010002030003010000000000000000000006070405080103090
2ffc4003c1000010304010205020305040b000000000102030400050611120721081314223141611516
3209182353715196a1d417243342445263818491a3ffc40015010101000000000000000000000000000
00001ffc4001511010100000000000000000000000000000001ffda000c03010002110311003f00faa7
4a5281511b875057032516718dde246dd43626b462f92796bdda53e17a1befecdf63a07b54baaa1c8ac
f21deb6db1e4e30e4a655e53a6f22df695a1ae293d8bae484cbd8e3f28695ad8d1d03a0b7a94a50294a
50783d87c6fed541f427c6d74dfc45664fe31882aecbb9b30973d7eb61794d8690b4209e5c8f7db89ed
57ed7ccdfd9a588b76bf15dd6a7b814aad2dc9b6a77ede2173b6471ff00c71fd35f7a2be995294a214a
52814a52814a52814a52814a52814a52814a52814a52814a5281501bcd95a7fac960b8728a5f6a03bec
522197c24734f2495366471dba01e0b091f51ee3b9f56adf8e856490def54b42d319d4fa60b6c2560a9
1ee20a799d77ee08036760ec683694a52814a52815c51e06f11771ff00135e29dd5a34cfe636d2cad29
3c4871f98f7104fd5295b7bfeb5daf546f40ec28b5f58baff002400172327880fbb675f85c5707db5fc
63aff1a2af2a52944294a50294a5060deef5071bb34ebb5ce5370add0595c89325d3a4b4da0152947ec
003582bcd6c8de456cb0aee0da2f5728aecd8b056950756cb7c39aca48da40f3503dda3eefb1d41fc4a
093fe8e6096b9fa3192584dc3cb27621fe2b17cfdebfdce1be5f4e3cb7db75adc87a7f1a2f8a8c232bb
6636d32ec9b15e9abcdee2410953cb0ab72632643e94fb95c50e04059de92ae3d81a0b4ad9935b2f567
76e9064fa984d2de6dc5a10ae495b4b521d414eb9724ad0a494eb7b046aab7b078aae9ce4f93b38f5ba
6df5dbc38e32d98ce62b7568b45e514b4a714b8c12d21452af7aca53ed5127409191d1af53f9e7ac607
316819537e8c2b7c797e1707d470df6e3e7799bd76e7cfebbac5c66cb748be213ab37336e9888532c16
26a1caf2cb6dc871b371e686dc50e2549f31bdf73c79a77f228ab3efb7db7631669b76bbce8f6cb5c26
94fc99929c0db4cb691b2a528f600541adde22ba7d73b5df2e0ddf56c3166b7bf75988996f9319e10d9
04b921b69c6d2b75b007ea6d2a07600dec6f95f18e94652bc6a643b3e213e6b76f72cf77b80ba5a9db4
ceba3f0a7477dc8b23cd74b13e42db43a7d5a38a14a4849510a045bbd60c9ee5d60e9e6751ec3d38bc7
16b0cbec6173be59dd893d325d8dc1b890d95a3cd74ba46d450381e0d805448d07474592dcc8cd48655
cd97501c42b5ada48d83ff00aaf6d45b05c898b8b322ca98f2e3ceb1b5163ca1263a9b4a94b8edb80b6
a3fac00ad123b052549f949ae4ee8c6211b36b858916ec6ae6ddc8e4d9235945fe443711126d99522e8
ca6279eaf63c3cd5b1a69249429b52884fca88edaa570afe48c9ba8fd3abe3373b7dd2e170c3e5d8f02
8e5a697ea64262dee2bb36736b6cf2e2e32dc4595a75c7c85927da48edcb1d8e063568896bb5c46e0db
e2a036c4764690da47c002833a94a502b06f77db76356a9373bb4f8d6cb7464798f4b96ea5a69b4ff6a
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6ac3d2842ee716f998dcd798e44c2838c38fb5e54182bd6898b176a4b7f274b5971dd120b8476a0c3fc
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2a345690a7a4cb735bf2d96500add5e81f6a013f5f8aaea1673d41be65d71c00231fb65fed90e34f9d9
032a75e65519f5ba8694c44568a5d263bdb4adc525bd20edde5c44e30fe9a5a71196f5cb948bc643210
1126fb74587a63c3fe5e5a01b46fbf96d84a01f848a08faa166fd4b58331d7fa7d8c2b7fea919c4aef3
2d3db5cdd49288892396d2d95b9a20871a5022bd8e740f17b6f952b1665cc32f8c8f6ddece78beff752
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4b6495c4faf7515b43eae827556126e51156f13c4a60c12df9c250707945bd6f9f2deb8ebbefe2b2149
0a0410083d883f5ae67ebde11626732e916009b7b56dc0f2ac9e5c9bdc08ea2d4696f350dc7d9616804
0e0ebc849520682ca7b8249d85ed8b752312ce5f94c63994d97207a2a8a24376bb833254ca87621610a
3c48d8f9ada5aaff006cbe2e722db7189705c092a872d315f4ba63be94a54a69ce24f0580b49293a202
81d7715cebe2bb05c73a7782d8f37c52c96fb066761be5adab43f6a8e88ce3e1e98cb2ec53c00e6dada
71cda0ec76debb547fa3fd40cd314cd3adb131ce975d33682bcfe6babb842bb408886dc316202d14487
90a2404a55b035ef037b07457555a2ff6cc8112976bb8c4b9222c9721c85447d2e865f6d5c5c697c49e
2b49eca49ee0f622b3eb9f3c16cd9572c2fa812e75bdcb4ce7f3fbf3afdbdd710e2e2b8a944a9a52d04
a5452494929241d6c122ba0e88ad7a91d56c2ad0e5c715c9a15f67b526316a547878bdcee11dd69c4e8
a4bb1e3ad0769241015b1f5d56b98f12f824661b690ce6250da4253cf09be295a035dc988493f73deac
5caf268386e3971bddc54e08705953ce259415b8bd7c21091dd4b51d25291dc9207d6a1171ebfd86d79
23d6b7adb77f4b0e6c5b5dc6f2965b30add3a4793e4c6795e672e6af50c0da12a424b8392850696c5d7
ee9be3500c2b640cb62c62f3b21494e117c254e38b538e2d44c424a94b5294493b249ad87ef3b837f27
2ffee3deff00c9d4ff0017ca61e5b01f950d2f3463ca7e13ec4847171a79a70a16950d9fa8d8209052a
4a86c106ab3c5fc491cca4a5769e9a66d26cc6e0fdbcdf4b56f4c3496642e3bae9dcc0e79695b6bd9e1
bd249093f14566fef3b837f272ff00ee3deffc9d3f79dc1bf9397ff71ef7fe4eb12d1e29f0dcb2c16fb
862689b99ccb84b9d0e2da2c463bb29c544584beb254f25b42005b2b0a5ad3b4bec91fad20e4dd7c4ce
2162878ac9b9b575b6a6ff007c5e3c96e5c4f297066252b2a4c90a50e29f66b9a7924f24ab7c0f201f8
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4a52814a5283e53f40f3732ff6ae64ae11fc3b85e6f76c0bf3bb7169b7b81f8ee0fa74e93f4e43fb3bf
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\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
Draw the product:
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(f)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
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\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
Draw the product:
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f0 \b1 \fs22 \cf1 \i0
24.\u160\'3f
}
}
{\f0 \b1 \fs22 \cf1 \i0
Problem 11.40
\par
}
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
Predict the products from each of the following reactions.
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(a)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
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0b23c68624500965c8c32b1c0c8e735b9e1ed3e5d27c35a569d70c8d35a59c5048d19254b2205246707
1915a54500145145001451450014514500473451dc42f0ca8af1c8a55918643023906a9e8fa2e9da069
f1d8697691db5ba0e150753ea4f527dcd14500685145140051451400514514005145140051451400514
514005145140051451401ffd9}}
\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
Draw the product:
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(b)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
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4a8ee77511b01d174a05294a05294a05294a05294a05294a05294a05294a05294a05294a05294a05294
a05294a0fffd9}}
\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
Draw the product:
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(c)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
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4141414141414141414141414141414141414141414141414141414141414141414ffc0001108003a00
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\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
Draw the product:
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
(d)
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
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\par
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
Draw the product:
\par
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
\u160\'3f
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
{\f4 \b0 \sb200 \fs18 \cf1 \i0
89504e470d0a1a0a0000000d494844520000000100000001010300000025db56ca00000006504c5445c
0c0c00000002bd7a1a60000000174524e530040e6d866000000097048597300000b1300000b1301009a
9c180000000a4944415478da6360000000020001e527defc0000000049454e44ae426082}}
89504e470d0a1a0a0000000d4948445200000226000001cc0103000000db37f17c00000006504c5445c
028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a1
5028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a15028140a8542a
15028140a8542a15028140ae55f25d305744e058cec8644c60000000049454e44ae426082}}
\par
}
}
{\li0 \f4 \b0 \ql \ri0 \fs18 \cf1 \i0
}
}
}}

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