UNIVERSITY OF THE WEST INDIES - CAVE HILL CAMPUS SEMESTER 1, 2018-2019

CHEM2705 INTERMEDIATE ORGANIC CHEMISTRY Dr. J. BADENOCK

STEREOCHEMISTRY – ASSIGNMENT #1 ANSWERS

SUBMISSION DEADLINE: SEPTEMBER 25, 2018 BY 3:00 PM
TOTAL MARKS = 36 MARKS

1. i. The specific rotation of optically pure sucrose is 66.37° clockwise. What would be the
expected observed rotation for a solution of 1.08 g of sucrose in 100 mL of water
measured in a 400 mm polarimeter tube?

[] = observed
cxl
observed = [] x c x l
= + 66.37 x (1.08/100) x 4 dm
= + 2.87o
[3 marks]

ii. The specific rotation of (S)-glyceraldehyde is -8.7° and (R)-glyceraldehyde has a specific
rotation of +8.7°. What is the optical purity (% ee) and percentage composition of an
enantiomeric mixture of glyceraldehyde with a specific rotation of -7.2°?

% ee = []enantiomeric mixture x 100

[]pure enantiomer

% ee = 7.2 x 100 = 83% excess of the S enantiomer

8.7

Therefore %S enantiomer = 91.5%; %R enantiomer = 8.5%

[4 marks]

2. Consider compounds I and II below:

2
CHO H CHO
HO H R
H HO OH H 3 OH 1
= = 2
HO H HO H
OHC CH2OH 1 S
CH2OH CH2OH
3
I
2
CHO HO CHO
1 S H HO
HO 3 H HO H H
2 = = OH
HO S H H
1 OHC CH2OH
CH2OH CH2OH
3
II

i. Convert I into a Fischer projection.

ii. Convert II into a Newman projection.
iii. For both compounds, I and II, determine the configuration (R or S) for every chirality
center.
iv. Are I and II the same compound, enantiomers or diastereomers? DIASTEREOMERS.
[9 marks]
UNIVERSITY OF THE WEST INDIES - CAVE HILL CAMPUS SEMESTER 1, 2018-2019
CHEM2705 INTERMEDIATE ORGANIC CHEMISTRY Dr. J. BADENOCK

3. Draw Fischer projections for (2S,3R)-2,3-dibromohexane (label it as such) and all its
stereoisomers. Indicate from your structures.:

CH3 CH3 CH3 CH3

H Br Br H H Br Br H
H Br Br H Br H H Br
CH2CH2CH3 CH2CH2CH3 CH2CH2CH3 CH2CH2CH3
(2S, 3R) (2R, 3S) (2S, 3S) (2R, 3R)
A B C D

i. a threo compound – C OR D
ii. an erythro compound – A OR B
iii. a pair of enantiomers – A+B OR C+D
iv. a pair of diastereomers – A+C OR A+D OR B+C OR B+D
v. a pair of epimers – A+C (C-3) OR A+D (C-2) OR B+C (C-2) OR B+D (C-3)
Remember that only chiral centers should be shown as crosses in the projection.
[10 marks]

4. When III is treated with a strong base, only one elimination product is observed. Yet, when
IV is treated with a strong base, two elimination products are observed.
Explain these observations by drawing each compound in the chair conformation favoured
for elimination and showing the likely mechanism. Be sure to show the product(s) that result
in each case.

T Base
H
=
H H
B B Cl H H
H3C Cl
III
MECHANISM IS E2; ONLY ONE PROTON WITH NECESSARY
ANTI-PERIPLANAR RELATIONSHIP TO Cl LEAVING GROUP

B Base H Base
H
T H3C
Cl H H
B H Cl
IV

MECHANISM IS E2; TWO PROTONS WITH NECESSARY

ANTI-PERIPLANAR RELATIONSHIP TO Cl LEAVING GROUP
[10 marks]