CHM 2211C Lesson 1: Organic I Review ey
1. Provide an ITUPAC name for each of the following compounds
0y 84 4-Arivromopanian - 3-0)
Br
)( Br b
)
CHy C /NH,. cn, B) A-emmgi- Da- dimednglegtishesang
\
cn‘. i He” -
Hyc” O CHj NO, C) J-nidrobuban- S-amine
d d) A edngi-B-gdveny ~ U emabing
CHy CHjy \)CH; CH; P endana
H:,C/‘\fi/(\n/H BES XN ) R-crlore-H-mettey ool - Y-enoie
OH o
o o.aigd
o
L3 20 e At Prepy ) tutie b anong
Cl
g \ \/\ H:,COC(CHJ);, Q) LM - Weme -~ B - G he Ay
VNaw- 3. ene
clOCH 2CHa
CH ) V-omeg
ropyl~ B - mavn WHe s an
H-one
L) - medmgii g 2,2 divn ety A ND) ENcle
e Aane
2. Draw the three non-equivalent resonance structures of the cyanate anion, OCN". Circle the structure
which is considered the major resonance contributor. V=" om rmore EN elermendt
[é—zc-u.] Lé=e=n]
1\ ? -2 ? v 4
3. Draw the resonance structure produced by the following electron shifts. Be certain to include all
appropriate formal charges.
% i CHs F
N
2 Loy N2
+
LcH
-
O <« % 4 H3C/ \/ \CH3
& € (S q:
ny© .\,/cu\
4. Draw the resonance structures for each of the following compounds. There are 2 resonance structures for
each of the following structures. ——
)X cn 3 CD -3 NH 2 ¥
$ Cl:l\'\z. x
<4 Ao Py
e L:z“z_
(€2 \ SvY
2 CW 3
, 5. Mark cach chiral center in the following molecules with an asterisk(*), If the compound has no chiral
centers, write achiral below the structure,
CHy
™ S
"“c/j) » n/ r/CH‘ , ’/ o > i" —
[+ &H oy Ao \
HyC ; I o >
1 eyvral cemrer Y ehniral cenvery
6. Assign R or S to the chiral centers in each of the following compounds
3
CHj COM 'j .3
WH 4 WPty 4 PR S O
HsC3 cHy 4 § v
Z ' 2 \
3 : S . T
L
HsCp > e Hs - C (& =
= \ ol U B—HAH 4 Z a2\ >
§HC” Yg, 3 * VcoH
2Hs 1
CaHy
=-CHy.
| BAw
>= z
K
s =
..~*
s ! £y
w ery— 3 3 . .
' =/ % . [ 2,
7. For each of the following reactions, write the major organic product. Each numbered set of reagents
above or below the arrow represents a completely separate reaction. For multistep reactions, only the
final product is necessary.
CH; Br,
e 20 2> ho.\n%cna-\-'\ on
A -
Hac/\/\/
GHy S22
NBS
o /W 2° atgic aloaenadion
S
HSCH,CH,
Cl O(s cnicig SN
Solvolngis Tocemic Mix dure
Me
CHs Na' ‘N
: )\ Na'N, morasic N 3",):\ S -inversion
, oF
8l Cts DMF eL ~ <
n contx.v‘..a_“ on
CH,CH,SH
® | &
—_—
promores e\irminclion
Z aitrsev's Rule
P NaoH | @
2 CH,OH
cHa n ;
€ei¥ner W elirminayed
1. Provide an ITUPAC name for each of the following compounds
0y 84 4-Arivromopanian - 3-0)
Br
)( Br b
)
CHy C /NH,. cn, B) A-emmgi- Da- dimednglegtishesang
\
cn‘. i He” -
Hyc” O CHj NO, C) J-nidrobuban- S-amine
d d) A edngi-B-gdveny ~ U emabing
CHy CHjy \)CH; CH; P endana
H:,C/‘\fi/(\n/H BES XN ) R-crlore-H-mettey ool - Y-enoie
OH o
o o.aigd
o
L3 20 e At Prepy ) tutie b anong
Cl
g \ \/\ H:,COC(CHJ);, Q) LM - Weme -~ B - G he Ay
VNaw- 3. ene
clOCH 2CHa
CH ) V-omeg
ropyl~ B - mavn WHe s an
H-one
L) - medmgii g 2,2 divn ety A ND) ENcle
e Aane
2. Draw the three non-equivalent resonance structures of the cyanate anion, OCN". Circle the structure
which is considered the major resonance contributor. V=" om rmore EN elermendt
[é—zc-u.] Lé=e=n]
1\ ? -2 ? v 4
3. Draw the resonance structure produced by the following electron shifts. Be certain to include all
appropriate formal charges.
% i CHs F
N
2 Loy N2
+
LcH
-
O <« % 4 H3C/ \/ \CH3
& € (S q:
ny© .\,/cu\
4. Draw the resonance structures for each of the following compounds. There are 2 resonance structures for
each of the following structures. ——
)X cn 3 CD -3 NH 2 ¥
$ Cl:l\'\z. x
<4 Ao Py
e L:z“z_
(€2 \ SvY
2 CW 3
, 5. Mark cach chiral center in the following molecules with an asterisk(*), If the compound has no chiral
centers, write achiral below the structure,
CHy
™ S
"“c/j) » n/ r/CH‘ , ’/ o > i" —
[+ &H oy Ao \
HyC ; I o >
1 eyvral cemrer Y ehniral cenvery
6. Assign R or S to the chiral centers in each of the following compounds
3
CHj COM 'j .3
WH 4 WPty 4 PR S O
HsC3 cHy 4 § v
Z ' 2 \
3 : S . T
L
HsCp > e Hs - C (& =
= \ ol U B—HAH 4 Z a2\ >
§HC” Yg, 3 * VcoH
2Hs 1
CaHy
=-CHy.
| BAw
>= z
K
s =
..~*
s ! £y
w ery— 3 3 . .
' =/ % . [ 2,
7. For each of the following reactions, write the major organic product. Each numbered set of reagents
above or below the arrow represents a completely separate reaction. For multistep reactions, only the
final product is necessary.
CH; Br,
e 20 2> ho.\n%cna-\-'\ on
A -
Hac/\/\/
GHy S22
NBS
o /W 2° atgic aloaenadion
S
HSCH,CH,
Cl O(s cnicig SN
Solvolngis Tocemic Mix dure
Me
CHs Na' ‘N
: )\ Na'N, morasic N 3",):\ S -inversion
, oF
8l Cts DMF eL ~ <
n contx.v‘..a_“ on
CH,CH,SH
® | &
—_—
promores e\irminclion
Z aitrsev's Rule
P NaoH | @
2 CH,OH
cHa n ;
€ei¥ner W elirminayed
