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Organic Chemistry Exam II: Stereochemistry and Isomers Practice, Exams of Organic Chemistry

Kennesaw State University (KSU)Organic Chemistry

A chemistry exam focusing on organic chemistry concepts, particularly stereochemistry and conformational analysis. It includes multiple-choice questions and free-response problems covering topics such as stereoisomers, enantiomers, diastereomers, newman projections, and chair conformations. The exam assesses students' understanding of stereospecific nomenclature and their ability to identify and analyze different types of isomers and conformers. It also tests their knowledge of optical activity and meso compounds, providing a comprehensive evaluation of their grasp of fundamental organic chemistry principles. The exam is designed for students to apply their knowledge of stereochemistry to solve problems and demonstrate their understanding of the spatial arrangement of atoms in molecules. The free-response section requires students to draw and analyze newman projections, chair conformations, and fischer projections, further enhancing their problem-solving skills in organic chemistry.

Typology: Exams

2023/2024

Available from 06/01/2025

Usvah-Hasan
Usvah-Hasan 🇺🇸

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Relative Energy vs. Bond Rotation
CHEM 3361/02 EXAM II Spring 2024 TOTAL POINTS 104
TURN IN ONLY THE FREE RESPONSE ANSWER SHEET AND THE BUBBLE SHEET. Keep this exam.
Record the following Version on the bubble sheet: A
Part I. Multiple Choice. Record your answers on the bubble sheet. (70pts, 3.5pts/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 methyl group and ______ to
the ethyl group.
a. anti, gauche b. gauche, anti c. gauche, gauche
d. anti, anti e. eclipsed, gauche
2. What structure below shows the same conformation as that shown above?
3. The conformer shown above corresponds with what position on the energy diagram above?
A. B. C. D. E.
4. In the conformation shown at right, the ethyl group is __________
to the methyl group and _________ to the deuterium atom.
A. anti, eclipsed B. gauche, gauche C. anti, gauche
D. gauche, eclipsed E. eclipsed, gauche
A
.
B.
C.
D.
E.
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 Spring 2024 TOTAL POINTS 104 TURN IN ONLY THE FREE RESPONSE ANSWER SHEET AND THE BUBBLE SHEET. Keep this exam. Record the following Version on the bubble sheet: A Part I. Multiple Choice. Record your answers on the bubble sheet. (70pts, 3.5pts/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 methyl group and ______ to the ethyl group. a. anti, gauche b. gauche, anti c. gauche, gauche d. anti, anti e. eclipsed, gauche
  2. What structure below shows the same conformation as that shown above?
  3. The conformer shown above corresponds with what position on the energy diagram above? A. B. C. D. E.
  4. In the conformation shown at right, the ethyl group is __________ to the methyl group and _________ to the deuterium atom. A. anti, eclipsed B. gauche, gauche C. anti, gauche D. gauche, eclipsed E. eclipsed, gauche

A

B.

C.

D.

E.

  1. A boat conformation, like the one shown at right, is less stable than a twist- boat because: I. There is a flagpole interaction between axial hydrogen atoms. II. One of the bond angles is approximately 120°. III. Two of the bonds are rotated to be eclipsed. A. I and II B. I and III C. II and III D. All of the above.
  2. What is the maximum number of stereoisomers possible for the structure shown at right? A. 2 B. 4 C. 6 D. 8 E. 16
  3. What is the maximum number of stereoisomers possible for the compound shown at right? A. 2 B. 4 C. 6 D. 8 E. 1
  4. What is the correct stereochemical description for the structure shown at right A. R B. S C. 2R, 3S D. 2R,3R E. 2S, 3S
  5. What is the correct stereochemical description of the structure shown at right? A. 1R, 4S B. 1 S, 4R C. 1R, 4R D. 1S, 4S E. There are no chiral centers.
  6. What is the correct stereochemical description of the structure shown at right? A. 1R, 2 S B. 1S, 2 R C. 1R, 2 R D. 1S, 2 S E. There are no chiral centers.
  1. What is the correct stereochemical description for the structure shown at right? A. 2S,3R B. 2R, 3S C. 2S, 3S D. 2R, 3R
  2. Which of the following statements an R-enantiomer of a given compound is necessarily true? I. It will react with an achiral reagent identically with the S-enantiomer of that compound. II. It will exhibit rotation of plane polarized light. III. It will have the same boiling point as the S-enantiomer of that compound. A. I only B. II only C. III only D. All of the above are true. E. None of the above are true. For Problems 1 8 & 1 9 , consider the following structures.
  3. Which of the above compounds is a meso compound? A. I only B. II only C. III only D. All of the above are meso compounds. E. None of the above are meso compounds.
  4. Which of the above compounds would be optically active (rotate plane-polarized light)? A. I only B. II only C. III only D. All of the above. E. None of the above.
  5. (S)-(+)- 2 - octanol has a standard rotation of +10.0°. A reaction of 2-bromooctane with water produced a sample of 2-octanol with an observed rotation of +8.4°. What is the composition of the product? A. 66%S B. 84%S C. 16%S D. 92 %S E. 76 %S

CHEM 3361/02 EXAM II Spring 2024 A NAME _____________________________________________ Free Response Answer Sheet. Part II. Nomenclature (12pts, 4pts/ea)

  1. Give the stereospecific structure of (S)- 2,3-dimethyl- 2 - pentanol 2. Give the stereospecific structure of (R)- 3 - bromocyclopentene
  2. Name the following compound stereospecifically. Part III. Essay (22pts)
  3. Complete the other chair conformation of the compound shown below. Show all the hydrogen atoms. Circle any groups undergoing diaxial interactions with the isopropyl or the methyl group on either structure and identify the more stable and less stable conformers. (10pts)