Organíc Chem¡stry 1

Exam 1, Ch 1-4 Fall 20L7

Name
/60l /4.o | /1oo
Note; Electron pairs might not be shown. Formalcharges Ch L.2.4 I Ch3l Total
are 0 unless ind ica ted.

1. Consider the four compounds below: (4 pt)

AB c D
o c¡
D +l ô -l O O
ìl hl +t -l
o- N. *cH? :O - N:CH2 o-N-cH. O::N-OJ,

á) Which compound{s) if any contain positively charged O? C

b) Which compounds(s) if any conta¡n negative N? ho he
c) Which compound(s) if any conta¡n positive C? C
d) Which compound(s) if any contain positive N? C" i

2. Draw all the neutral organic structures that obey Lewis rules (and HONC rules) with the formula: C3H6O (2

Ant o
t
ct\roù [\------l
o*' Cú¡ r+o
.þ*o ol' -' + \:/ + z'F"^r \
.D

u '-\
-, tl ^ u'--\.u, ,,,--\ û+l )C= .l !u-
3. Carbon dioxide can sati!¡/ the
il
Lewis octet rule in two ways as shown below. Circle the more stable version
and briefly explaln the reason for your choice. (2 pts)

o:c:o .ì- .fI

/"'1"-*- -1b.-c;ö
..
r No 1r,,.-^/ cl,'.trr or.-
\'- - ----./
I
r "4tf V(¡r¡s,,oi^\ à ,,y,6_..¿ ,+^W
4. Based on the HONC rules, can the molecular formula Cu HzO exist as an organ¡c chemical? (2 pt)

r/ YES ) NO lfyes, draw a likely structure. \1.--r'

,' '-
: (_r - o^.
\J ll
l'l
-
W rL-
ac= o
5. For the molecular shapes below, predict the most likely direction of dipole ( + + -) (2 pt)

1-D:é-=--'
H

/t2
 Organic Chemistry 1
Exam 1, Ch 1-4 Fall 2017

6. Determine the hybridization of the atoms indicated wìth each of the molecules below: {5 pt)

,) N_5É oto r;j' c)N-sp- d)o5Ë- "tc ef

H,C-NH ¡.to& |
.--":'
......-o-
tr
7 Draw a|I the const¡tutiona| -n.î:t5iîi'ilÏ,#"iÏ"'

V\rr\
I
-\-,'-.t-t
\_-/ +^
i-¿xr..n..p 2-'.Å,1\p".la^, t-,s -J', 2-' ¿ - i'-Jþ[b"]o*"
-.,tt6{b"t"w
8, Circle where the lone pairs live in the compounds below and ¡nd¡cate their hybridization. (4 pts)

f- =P) Â"'
(ö,,',

Hybrid ization (s )
rf
9. Draw the equ¡valent abbreviated bond line structure¡ for the condensed structures below: (4 pts)

a) (CHr)TCCH,CH,CH{CHr)7
-l-f'\

b) (CH¡)u CHCHzCHzoH \ ------^

/ \-.-- o+l
10. ldentify the functional groups represented by: (4 pt)

\o--^\-/'
é
<1-h"ø ald"l
#q
:. a.'- { C v-p^^ o

11. Draw specific examples ofthe functionalgroups (4 pt)

( c,
"o'.-'rll'
c \
a)amide b) amine c) ester d) acid ch loride
il¿J \ ( *
.= r) NH, C=o
,.,." C=r>
l)\ -_o
t9.
Organic Chemistry 1
Exam 1, Ch 1-4 Fall 2017

2. Prov¡de the IUPAC name lor the compou nds below pts each, 12 pts tota l)

_-.^_Ø)

t-+ ' \/'Y'

j*.ì\",-r -z- ;,\\^,Å
9 -oll ì*i.-r 1.'t""r., "n*t *.
/<l(
._,Xp*, L

s* ¿+- ( r . -^,+t-( ) - r. - - J:,.*#. (l L, ^r -lJ

"+i^.q s
I3.
h cøt¿'
Draw the structures named below: (3 pts eaih, 6^{
pls) b..q.lo [3 r,o] horl*
1-cyclohexyl-41 lmethylethyl)octa ne 3-isopropvlbìcyclot3.2.0l heptane

X
V
L4- tol a-c, answer the following questìons us¡ng the energy diagram below (right). The plastic models are
available if you choose. (5 pts total) f-)
a) lD the posit¡on where the butane structure is anli !' ?,-,
b) lD the position where the butane struclure is gauche l-L
c) Which position are the methyls on C2 and C3 of butane eclipsing each other? *ì^
d) Using the Newman project¡on template below (left), draw the structure associated
with an anti butane configuration. (2 pt)

(l-l: A

-tt6
u -11å
-18ø
(-\

A1 - te4
CH: '.È -re6

/23 - r30

-r3Ê