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Chem 3361, Organic Chemistry I Exam II, S19_Kennesaw state university, Dr. Animesh Aditya, Exams of Organic Chemistry

It's a solved past exam of Chem 3361, Modern Organic Chemistry I Exam II, Spring 2019, Kennesaw State University, by Dr. Animesh Aditya. It includes topics like stereochemistry, R/S configurations, enantiomers, diastereomers, conformers etc.

Typology: Exams

2018/2019

Available from 06/01/2025

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Relative Energy vs. Bond Rotation
CHEM 3361/02 EXAM II NAME ______________________________________________________
Spring 2019 TOTAL POINTS 108
Record the following number on your Scantron next to your name: _________
Part I. Multiple Choice (72pts, 4.5pts/ea)
For Problems 1-3, consider the structure shown at right and the Energy Diagram below
1. In the conformation shown at above, the phenyl group is ______ to the ethyl group and ______ to
the methyl group.
a. anti, gauche b. gauche, anti c. gauche, gauche
d. anti, anti e. eclipsed, gauche
2. The conformer shown above corresponds with what position on the energy diagram above?
a. I b. II c. III d. IV e. V
3. What structure below shows the same conformation as that shown above?
a. I b. II c. III d. IV e. none of the above
I.
II.
III.
IV.
V.
pf3
pf4
pf5

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15 35 55 75 95 115 -100 -50 0 50 100 150 200 250 300 350 400 450

Relative Energy vs. Bond Rotation

CHEM 3361/02 EXAM II NAME ______________________________________________________

Spring 2019 TOTAL POINTS 108 Record the following number on your Scantron next to your name: _________ Part I. Multiple Choice (72pts, 4.5pts/ea) For Problems 1- 3 , consider the structure shown at right and the Energy Diagram below

  1. In the conformation shown at above, the phenyl group is ______ to the ethyl group and ______ to the methyl group. a. anti, gauche b. gauche, anti c. gauche, gauche d. anti, anti e. eclipsed, gauche
  2. The conformer shown above corresponds with what position on the energy diagram above? a. I b. II c. III d. IV e. V
  3. What structure below shows the same conformation as that shown above? a. I b. II c. III d. IV e. none of the above

I.

II.

III.

IV.

V.

For Problems 4 & 5, consider the structure shown below.

  1. Rank the above from highest to lowest energy. A. I > II > III B. II > III > I C. II > I > III D. I > III > II E. III > II > I
  2. In which of the structures above are there eclipsed bonds? A. I and II B. II and III C. I and III D. all of the above have eclipsed bonds E. none of the above have eclipsed bonds
  3. What is the maximum number of stereoisomers possible for the compound shown at right? A. 2 B. 4 C. 8 D. 16 E. 6
  4. From the structure shown at right , it can be determined that the compound shown I. has an S configuration. II. has an R configuration. III. will exhibit a levorotatory rotation (-) of plane polarized light. IV. will exhibit a dextrarotatory rotation (+) of plane polarized light. a. I only b. II only c. I and III d. I and IV e. II and IV
  5. An optically active compound has an S configuration with an absolute rotation of (+) 50.0 under standard conditions. A sample prepared in the lab is found to exhibit a rotation of (-) 40.0 under standard conditions. It can be deduced that the compound prepared is A. 40% R B. 90% S C. 90% R D. 80% S E. 50% R
  6. The structure shown at right is a. R b. S c. achiral

C

HOCH 2 CCH 3

HO H

O

  1. Which of the following compounds is a meso compound? a. I only b. II only c. III only d. I and II e. I and III
  2. Which of the compounds shown in Problem 1 5 above would be expected to rotate plane polarized light? a. I only b. II only c. III only d. I and II e. I and III Part II. Nomenclature with Stereochemistry (9pts, 4.5pts/ea)
    1. Give the stereospecific IUPAC name of the structure shown at right.
    2. Give the stereospecific structure of (S)-3,3-dimethyl- 2 - pentanol.

Part III. Essay (20pts)

  1. Show the LESS STABLE chair conformation of the structure shown below and explain its instability using specific repulsion arguments. ( 9 pts)
  2. Consider the structure below. Complete the Newman Projection at right to show the present orientation of the atoms. (4.5 pts) Also complete the wedge-line-dash representation below to show the orientation of the atoms after 120° rotation to place the deuterium atom (D) ANTI to the chlorine atom. (4.5 pts) (Continued on next page.)