CHM 2210-11 Examination 3 A March 22, 2024
INSTRUCTIONS (Read carefully}): This examination has three pages of problems, 1 double sided
answer sheet, a periodic table and 1 blank sheet for scratch work. Read each questions carefully.
Write your answers in the spaces provided on the answer sheet. There is a total of 110 points.
REGRADE POLICY: If you have a question about the number of points that you earned on your
graded exam answer sheet, do not make changes or additions to your returned, graded answer
sheet. Bring it to Dr. Krishnan after a lecture or during an office hour, preferably within 2 weeks after
it is returned.
1. [24 pts] Complete the following reactions supplying the missing reactants, reagents or products
and showing correct stereochemistry where applicable. If more than one organic product forms,
indicate which, if any, is the major product. Where applicable show both enantiomers. Write NR
if no reaction takes place.
H H HBr
> 3
H,C cn, O5¢
(4]
OH
- nal Acetone N ?
Br ? 0
0—C—CHs
{c)
PN = > A
H, oo
(d>\>\& Hac:»@—-sozm —3 P
OH
{e) el
qfir 4 CHOH ————— 7
{f) /L(’\ HCE
o
OH
2. (A) [8 pts] Name the compound given below according to substitutive IUPAC nomenclature.
(Indicate stereochemistry where appropriate, R/ S designations must be provided)
u.ltl1<
H Cl
O
, (B) [4 pts] Non-sticky nature of the frying pan used in kitchen is due to the coating of polymer
Teflon. What is the structure of the individual units (monomer structure)?
(C) [8 pts] Write structural formulas for (a) 2-Butanone and (b) oxirane
3. Outline an efficient synthesis of the following compounds from the indicated starting material
and any necessary organic or inorganic reagents:
{A) [8 pts] Starting from cis-2-methylcyclpentanol synthesize cis-2-methylcyclopentyl acetate
{B) [8 pts] Starting from optically pure (R)-2-pentanol synthesize optically pure (R)-2-
bromopentane.
4. Choose the right answer (a/b/c/d) from the following four options provided in each case
(A) [4pts] What is the major product of the reaction shown below?
CH,
H Br NaNy, DMF
HyC—— H 25°%c
CH,CH,
(2) CH, (b) cH, () CH, (d) CH,
H N3 Ng—r—-H H=——p— N Ny——H
H,C H H,C H H cH; H CH,
CH,CH, CH,CH, CH,CH, CH,CH,
{B) [4pts] For the following reaction, the product(s) formed is/are
M 1. PBr,
2.H,0
(a) diastereomers (b) meso compounds (c) enantiomer (d) racemic mixtures
{C) [4pts] The carbocation resulting from the immediate heterolytic cleavage of neopentyl chloride
is
(a) \5% (@) ._.%,_, @ @y ©
(D) [4pts] Total number of contributing structures showing hyperconjugation for the following
carbocation is
@
(a) 3 (b) &6 (c)9 (d)12
INSTRUCTIONS (Read carefully}): This examination has three pages of problems, 1 double sided
answer sheet, a periodic table and 1 blank sheet for scratch work. Read each questions carefully.
Write your answers in the spaces provided on the answer sheet. There is a total of 110 points.
REGRADE POLICY: If you have a question about the number of points that you earned on your
graded exam answer sheet, do not make changes or additions to your returned, graded answer
sheet. Bring it to Dr. Krishnan after a lecture or during an office hour, preferably within 2 weeks after
it is returned.
1. [24 pts] Complete the following reactions supplying the missing reactants, reagents or products
and showing correct stereochemistry where applicable. If more than one organic product forms,
indicate which, if any, is the major product. Where applicable show both enantiomers. Write NR
if no reaction takes place.
H H HBr
> 3
H,C cn, O5¢
(4]
OH
- nal Acetone N ?
Br ? 0
0—C—CHs
{c)
PN = > A
H, oo
(d>\>\& Hac:»@—-sozm —3 P
OH
{e) el
qfir 4 CHOH ————— 7
{f) /L(’\ HCE
o
OH
2. (A) [8 pts] Name the compound given below according to substitutive IUPAC nomenclature.
(Indicate stereochemistry where appropriate, R/ S designations must be provided)
u.ltl1<
H Cl
O
, (B) [4 pts] Non-sticky nature of the frying pan used in kitchen is due to the coating of polymer
Teflon. What is the structure of the individual units (monomer structure)?
(C) [8 pts] Write structural formulas for (a) 2-Butanone and (b) oxirane
3. Outline an efficient synthesis of the following compounds from the indicated starting material
and any necessary organic or inorganic reagents:
{A) [8 pts] Starting from cis-2-methylcyclpentanol synthesize cis-2-methylcyclopentyl acetate
{B) [8 pts] Starting from optically pure (R)-2-pentanol synthesize optically pure (R)-2-
bromopentane.
4. Choose the right answer (a/b/c/d) from the following four options provided in each case
(A) [4pts] What is the major product of the reaction shown below?
CH,
H Br NaNy, DMF
HyC—— H 25°%c
CH,CH,
(2) CH, (b) cH, () CH, (d) CH,
H N3 Ng—r—-H H=——p— N Ny——H
H,C H H,C H H cH; H CH,
CH,CH, CH,CH, CH,CH, CH,CH,
{B) [4pts] For the following reaction, the product(s) formed is/are
M 1. PBr,
2.H,0
(a) diastereomers (b) meso compounds (c) enantiomer (d) racemic mixtures
{C) [4pts] The carbocation resulting from the immediate heterolytic cleavage of neopentyl chloride
is
(a) \5% (@) ._.%,_, @ @y ©
(D) [4pts] Total number of contributing structures showing hyperconjugation for the following
carbocation is
@
(a) 3 (b) &6 (c)9 (d)12
