Name

Section/TA CoV.
Read each question carefully. You may use one 3" x 5" notecard with
handwritten notes. No calculators or any other electronic devices are
necessary or allowed.
Please make your answer easy to find. Communicating your answer is as important as obtaining it.


1. The infrared spectra of 1-octanol and 1-decanol look extremely similar. Give two ways in which you could tell
the two alcohols apart using other spectroscopic methods. Be spec/^c. (5 points) Sy
vi oUU kt W Wou
ouVA \aOM. T- WUkVL iVoVKtU.
v\ uo-vXU
oWUa vV

'
O.WV- VMAW<V\ yvAiVtiWt
Give one^advantage that NMR has over NMR, and
one advantage that NMR C NMR. (5 points)
VtVvJtw Wv- Hvt/
d(.iV\vv^-V uVvcvtM
vv\ 0-
v!(V^tAV- \vA aAi^rv\^v/\ ?vovi^V\v^i
NiVUVl^^V cuUv\j



3. Predict the multiplicity (singlet, doublet, etc.) you would expect for each set of protons in the
molecule below. (8 points) ^
CHEM238B Winter
2012 EXAIVI2 100
points
specific. (5 points)
wvuxo^v w\Q.3\/VM:(<^
WVOOA.'^
V- d,tcfliWo\
\ oV
vv,o^woV 6^ AvH^vtvvv
-iVAVvV^\vwtM*r

a{has over
gia<2. C
O^JMVXAX MvVVf
{(KV Wy^ <- vaov e. vV\cv>| '
\a*\ VAWUJA.V . dvJK-tvtWV
(IVIOVA.V '^A^. WWVa-V Of-
;yV\\V\V\^ 0 s\ov\<v.\i
2.
3
7
4.


4.

Mg
MgBr
EtzO
O
1)
2)
Fill in the missing information for each reaction. Be sure to indicate geometry where appropriate.
(3 points for each box)

OSO4 (cat), 'BUOOH
"OH, BUOH




HI04



r)ipM/6fiD

OH



(^O
X-O-H




5. Give an arrow-pushing mechanism for the reaction shown. (8 points)




o
+

H
O
OH
1) CH3C
H2MgBr
2) H3O*

6. You reacted methylmagnesium bromide with acetone in ether, followed by acid workup.
What would you look for spectroscopically to determine whether you made the desired product?
Be specific and give more than one spectroscopic feature. (5 points)
^W uovJiU W a
n (kv/^vLVvd 1^00 cvAA-\ HOVA^OLVVM") Wvt. c4vVo\A^\
^ ^ W A ^ w o < x V < ^ ^
s V f 3 V l ^ \
y'oSJVVoV^ o^VQawA 'V.T YX<A (X.\Ai VV\ CVOWO.U vv\
VVc ^' ^r vynA WH\ p r ^j Oud-
7. Propose a synthesis for the following compounds. Your starting materials can contain no
more than four carbons. There may be more than one way to make each one. (5 points each)
___ _K f u - cHv lAO t?
O
V) 6\\
OAvCu + ^ ^ "LCJ^u^Wl
\x

HQ
X


<



8. Question 14.31 in your textbook reads as follows:
A compound having the molecular formula C22H32O2 was isolated in 66% yield in the
following reaction. Suggest a reasonable structure for,this compound. What other organic
compound is formed in
this reaction? Please do
this problem. (5 points)
HC=CH2
6
<

OH
OH
0

t^
v
II Cl2(Cy3P)2Ru
CHCeHs
^^=Y^C""2(CH2)7CH=CH2
"O

Provide a structure tiiat is consistent with the following spectral data. Show your reasoning for
possible partial credit. (20 points)
MASS SPECTRUM
40 60
m/z
INFRARED SPECTRUM

10
0
100



T f-
2 . 0 1 . 0 ppn 3. 0
4 HV
[6]










[2]
[1+
1]

he numbers in bracl<ets represent the peal< integrations. The [1+1] signal is two
overlapping peaks - a multiplet and a singlet. The singlet disappears upon addition of D2O to
the sample.
Cy
4
ppm



[2
]