Organic Chemistry 1

Semester 2: 2022-2023

Homework 3
STEREOCHEMISTRY AT TETRAHEDRAL CENTERS
SOLUTION:
Question 1:

Question 2:
 Organic Chemistry 1
Semester 2: 2022-2023

Question 3:

Question 4:

Question 5:

Question 6:
 Organic Chemistry 1
Semester 2: 2022-2023

Question 7:

Question 8:

Question 9:

Question 10:
 Organic Chemistry 1
Semester 2: 2022-2023

Question 11: Draw tetrahedral representations of the following molecules:

(a) The 2S,3R enantiomer of 2,3-dibromopentane
(b) The meso form of 3,5-heptanediol
Question 12:
Identical molecules: b (S enantiomer), c (R enantiomer), d (S enantiomer).
Pair of enantiomers: a.
Problems:
1.

(d) This is a meso compound. This molecule has a mirror image (as do all things except a
vampire), but the original object and mirror image are superposable. Because it has stereocenters
and is superposable on its mirror image, this is a meso compound. Because of their mirror image
superposability, meso compounds cannot have enantiomers.
 Organic Chemistry 1
Semester 2: 2022-2023

2.