Deck 4: Organic Compounds: Cycloalkanes and Their Stereochemistry

Question 1

Circle all bridgehead carbons in the following structure.

Answer 1

Question 2

Exhibit 4-2
For each substituted cyclohexane below,draw its ring-flip isomer.Circle the most stable conformation.
Refer to Exhibit 4-2.

Answer 2

Question 3

Exhibit 4-1
Refer to the structure below to answer the following question(s):
Refer to Exhibit 4-1.Which of the labeled bonds are trans to bond b?

Answer 3

e

Question 4

Draw 7 constitutional isomers of a cycloalkane with the formula C₆H₁₂.Name each of the isomers you drew.

Question 5

Draw: cis-1-sec-butyl-2-ethylcyclopentane

Question 6

Draw: 3-cyclobutylpentane

Question 7

This question was omitted on the printed copy.This placeholder question is here to maintain the numbering system integrity between the printed copy and ExamView.Therefore,it has been marked "do not use on test" in ExamView's question information dialog.As a result,this placeholder question is automatically prevented from being chosen as a test question.

Question 8

The energy difference of 3.8 kJ/mol between gauche and anti butane corresponds to an equilibrium constant,K_eq,of approximately 1.9.Calculate the percentage of each conformer at equilibrium.

Question 9

Exhibit 4-1
Refer to the structure below to answer the following question(s):
Refer to Exhibit 4-1.Which of the labeled bonds in the structure are equatorial bonds?

Question 10

Draw: 1-chloro-2-isopropylcyclopentane

Question 11

Below are the two chair conformations of a 1,2,4-trimethylcyclohexane.Estimate the amount of 1,3-diaxial strain in each conformer and predict which conformer is most stable.

Question 12

Draw: 3,5-dicyclohexylnonane

Question 13

Exhibit 4-1
Refer to the structure below to answer the following question(s):
Refer to Exhibit 4-1.Which labeled bonds have a 1,3-diaxial interaction with each other?

Question 14

Draw the two stereoisomers of 1,3-dibromocyclobutane.

Question 15

Exhibit 4-3
The following question(s) refer to the structure of camphor shown below.
Refer to Exhibit 4-3.Circle all bridgehead carbons in camphor.

Question 16

Name:

Question 17

The original question was combined with #1.This placeholder question is here to maintain the integrity of the numbering system between the printed copy and ExamView.Therefore,it has been marked "do not use on test" in ExamView's question information dialog.As a result,this placeholder question is automatically prevented from being chosen as a test question.

Question 18

Exhibit 4-3
The following question(s) refer to the structure of camphor shown below.
Refer to Exhibit 4-3.Camphor is an example of a:

A)fused bicyclic molecule.
B)bridged bicyclic molecule.
C)fused tricyclic molecule.
D)bridged tricyclic molecule.

Question 19

Exhibit 4-2
For each substituted cyclohexane below,draw its ring-flip isomer.Circle the most stable conformation.
Refer to Exhibit 4-2.

Question 20

Exhibit 4-2
For each substituted cyclohexane below,draw its ring-flip isomer.Circle the most stable conformation.
Refer to Exhibit 4-2.

Question 21

Exhibit 4-4
Label each pair of compounds below as:
_____

A)conformational isomers
B)stereoisomers
C)constitutional isomers
D)identical

Question 22

(-)-Menthol can be isolated from the peppermint plant and is responsible for the characteristic flavor and taste of peppermint.The structure of (-)-menthol is: On the chair template provided below,draw the two chair conformations that are in equilibrium for (-)-menthol.

Question 23

Which of the following would have the smallest strain energy (kJ/mol)?

A)cyclobutane
B)cyclopentane
C)cyclohexane
D)cyclooctane

Question 24

In cyclopropane,which of the following strain types would be the least important in determining the overall energy?

A)angle
B)torsional
C)steric
D)All make a significant contribution.

Question 25

In general,5-alkyl substituents in 1,3-dioxane exhibit a smaller equatorial preference than they do in cyclohexane.To what might you attribute this observation?

Question 26

Consider the following table. Number of Carbon Atoms in Ring
Heat of Combustion per CH₂ (kJ)
3
696
4
686
5
664
6
659
What is the approximate strain energy per CH₂ for cyclopropane?

A)12 kJ
B)37 kJ
C)110 kJ
D)230

Question 27

D-Pinitol is an interesting hexahydroxy cyclohexane,whose structure is shown below. On the templates provided,draw the two chair conformations that are in equilibrium for D-pinitol.Circle the most stable conformation.

Question 28

In methylcyclohexane:

A)all carbon atoms are sp³ hybridized.
B)ring-carbon atoms are sp² hybridized and the methyl group is sp³ hybridized.
C)all bond angles are approximately 120°.
D)ring-bond angles are approximately 120° and the ring-methyl bond angle is approximately 109°.

Question 29

Consider the two methyl groups indicated with letters in the following molecular model. These two groups are:

A)A: axial B: axial
B)A: axial B: equatorial
C)A: equatorial B: axial
D)A: equatorial B: equatorial

Question 30

Which of the following would produce the greatest amount of 1,3-diaxial strain when substituted for Cl in the following structure?

A)CN
B)OH
C)C(CH₃)₃
D)CO₂H

Question 31

Consider the following table. Number of Carbon Atoms in Ring
Heat of Combustion per CH₂ (kJ)
3
696
4
686
5
664
6
659
Based on the data in the table,which of the following compounds would have the largest strain energy?

A)cyclopropane
B)cyclobutane
C)cyclopentane
D)cyclohexane

Question 32

What relationship exists between the following two structures?

A)identical molecules
B)constitutional isomers
C)stereoisomers
D)different molecules

Question 33

The two structures show below represent:

A)constitutional isomers
B)stereoisomers
C)cis-trans isomers
D)both b and c
E)a,b and c

Question 34

Exhibit 4-4
Label each pair of compounds below as:
_____

A)conformational isomers
B)stereoisomers
C)constitutional isomers
D)identical

Question 35

Exhibit 4-4
Label each pair of compounds below as:
_____

A)conformational isomers
B)stereoisomers
C)constitutional isomers
D)identical

Question 36

Exhibit 4-4
Label each pair of compounds below as:
_____

A)conformational isomers
B)stereoisomers
C)constitutional isomers
D)identical

Question 37

Exhibit 4-4
Label each pair of compounds below as:
_____

A)conformational isomers
B)stereoisomers
C)constitutional isomers
D)identical