Organic Chemistry 1

Semester 2: 2022-2023

Homework 3
STEREOCHEMISTRY AT TETRAHEDRAL CENTERS
Note: Your Group has to write the solution by hand (only 1 copy is needed) and convert it into a
PDF file when submitting it on Blackboard. Remember to write the full name and ID student
of each member in the group.
WE WILL HAVE A QUIZ 3 NEXT WEEK!!!

Deadline: 28/2/2023
● Test Book: Organic chemistry 9th by John McMurry
Question 1:Which of the following compounds are chiral? Draw them, and label the
chirality centers.
(a) 2,4-Dimethylheptane (c) cis-1,4-Dichlorocyclohexane
(b) 5-Ethyl-3,3-dimethylheptane (d) 4,5-Dimethyl-2,6-octadiyne
Question 2: Assign Cahn–Ingold–Prelog rankings to the following sets of substituents:

Question 3: Assign R or S configurations to the chirality centers in the following molecules:

Question 4: Assign R or S configuration to each chirality center in the following molecules:

 Organic Chemistry 1
Semester 2: 2022-2023

Question 5: Assign R or S configuration to each chirality center in the following biological

molecules:

Question 6: Assign R or S configuration to each chirality center in the following molecules:

Question 7: Draw chiral molecules that meet the following descriptions:

(a) A chloroalkane, C 5H11Cl (b) An alcohol, C6H14O
(c) An alkene, C 6H12 (d) An alkane, C8H18
Question 8: Eight alcohols have the formula C5H12O. Draw them. Which are chiral?
Question 9: Draw tetrahedral representations of the following molecules:
(a) (S)-2-Chlorobutane (b) (R)-3-Chloro-1-pentene
Question 10: Draw tetrahedral representations of the two enantiomers of the amino acid
cysteine, HSCH2CH(NH2)CO2H, and identify each as R or S.
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
 Organic Chemistry 1
Semester 2: 2022-2023

Question 12: Which of the following pairs of structures represent the same enantiomer, and
which represent different enantiomers?

Problems:

2. Draw a diastereomer of each structure