Puckered conformation of methylcyclobutane needs to be determined. Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The eclipsing strain is due to the nonbonding interactions of the groups and atoms. The molecules can be stabilized when it will remove eclipsing strain.

Question

5. Draw the two chair conformations ("ring filips") of trans –1- ethyl-4-methylcyclohexane to show the axial and equatorial substituents (including all hydrogens). Then determine which of the two conformations is more stable and why.

Answer 1

Question

Chapter 4, Problem 29P

(a)

Interpretation Introduction

Interpretation : Puckered conformation of methylcyclobutane needs to be determined.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The eclipsing strain is due to the nonbonding interactions of the groups and atoms. The molecules can be stabilized when it will remove eclipsing strain.

(b)

Interpretation Introduction

Interpretation : Puckered conformation of cis-1, 2-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

(c)

Interpretation Introduction

Interpretation : Puckered conformation of trans-1, 2-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

(d)

Interpretation Introduction

Interpretation : Puckered conformation of cis-1, 3-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

(e)

Interpretation Introduction

Interpretation : Puckered conformation of trans-1, 3-dimethylcyclobutane needs to be drawn. Also, the stability of cis and trans 1,2dimethylcyclobutane and cis and trans 1,3dimethylcylobutane needs to be compared.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

The conformers have the same molecular formula, but the spacious arrangements of the groups are different.

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5. Draw the two chair conformations ("ring filips") of trans –1- ethyl-4-methylcyclohexane to show the axial and equatorial substituents (including all hydrogens). Then determine which of the two conformations is more stable and why.

11. s) Draw the most stable conformation of 1,3-dichloro-2,4-difluorocyclohexane: 12. Which of the following represents the most stable conformation of 1,2,4,5- tetramethyleyclohexane? (one correct answer) CH b) CH HC H- H- CH HC CH, CH 6. Give IUPAC name for the following molecule. Include "cis" and "trans" designations if applicable. H2C-CH3 H -CH2 H- H Br

4. Which structure below represents the most stable conformation of cis-1-t-butyl-4-methylcyclohexane? A B D 5. The planar form of which ring would have bond angles close to the tetrahedral value, but is destabilized by eclipsing interactions (torsional strain)? Which of the following statements about conformations is FALSE? A) Conformations can be isolated and separated at room temperature B) Conformations are interconverted by rotation about o-bonds C) For butane the staggered anti conformation is the most stable D) For ethane the eclipsed conformation is the least stable 6. 7. Which of the following compounds has two chirality centers? .H H. H3C

Answer 2

Question

Chapter 4, Problem 29P

(a)

Interpretation Introduction

Interpretation : Puckered conformation of methylcyclobutane needs to be determined.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The eclipsing strain is due to the nonbonding interactions of the groups and atoms. The molecules can be stabilized when it will remove eclipsing strain.

(b)

Interpretation Introduction

Interpretation : Puckered conformation of cis-1, 2-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

(c)

Interpretation Introduction

Interpretation : Puckered conformation of trans-1, 2-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

(d)

Interpretation Introduction

Interpretation : Puckered conformation of cis-1, 3-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

(e)

Interpretation Introduction

Interpretation : Puckered conformation of trans-1, 3-dimethylcyclobutane needs to be drawn. Also, the stability of cis and trans 1,2dimethylcyclobutane and cis and trans 1,3dimethylcylobutane needs to be compared.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

The conformers have the same molecular formula, but the spacious arrangements of the groups are different.

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Answer 3

Question

Chapter 4, Problem 29P

(a)

Interpretation Introduction

Interpretation : Puckered conformation of methylcyclobutane needs to be determined.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The eclipsing strain is due to the nonbonding interactions of the groups and atoms. The molecules can be stabilized when it will remove eclipsing strain.

(b)

Interpretation Introduction

Interpretation : Puckered conformation of cis-1, 2-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

(c)

Interpretation Introduction

Interpretation : Puckered conformation of trans-1, 2-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

(d)

Interpretation Introduction

Interpretation : Puckered conformation of cis-1, 3-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

(e)

Interpretation Introduction

Interpretation : Puckered conformation of trans-1, 3-dimethylcyclobutane needs to be drawn. Also, the stability of cis and trans 1,2dimethylcyclobutane and cis and trans 1,3dimethylcylobutane needs to be compared.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

The conformers have the same molecular formula, but the spacious arrangements of the groups are different.

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Answer 4

Question

Chapter 4, Problem 29P

(a)

Interpretation Introduction

Interpretation : Puckered conformation of methylcyclobutane needs to be determined.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The eclipsing strain is due to the nonbonding interactions of the groups and atoms. The molecules can be stabilized when it will remove eclipsing strain.

(b)

Interpretation Introduction

Interpretation : Puckered conformation of cis-1, 2-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

(c)

Interpretation Introduction

Interpretation : Puckered conformation of trans-1, 2-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

(d)

Interpretation Introduction

Interpretation : Puckered conformation of cis-1, 3-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

(e)

Interpretation Introduction

Interpretation : Puckered conformation of trans-1, 3-dimethylcyclobutane needs to be drawn. Also, the stability of cis and trans 1,2dimethylcyclobutane and cis and trans 1,3dimethylcylobutane needs to be compared.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

The conformers have the same molecular formula, but the spacious arrangements of the groups are different.

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Answer 5

Chapter 4, Problem 29P

(a)

Interpretation Introduction

Interpretation : Puckered conformation of methylcyclobutane needs to be determined.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The eclipsing strain is due to the nonbonding interactions of the groups and atoms. The molecules can be stabilized when it will remove eclipsing strain.

(b)

Interpretation Introduction

Interpretation : Puckered conformation of cis-1, 2-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

(c)

Interpretation Introduction

Interpretation : Puckered conformation of trans-1, 2-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

(d)

Interpretation Introduction

Interpretation : Puckered conformation of cis-1, 3-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

(e)

Interpretation Introduction

Interpretation : Puckered conformation of trans-1, 3-dimethylcyclobutane needs to be drawn. Also, the stability of cis and trans 1,2dimethylcyclobutane and cis and trans 1,3dimethylcylobutane needs to be compared.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

The conformers have the same molecular formula, but the spacious arrangements of the groups are different.

Answer 6

Chapter 4, Problem 29P

(a)

Interpretation Introduction

Interpretation : Puckered conformation of methylcyclobutane needs to be determined.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The eclipsing strain is due to the nonbonding interactions of the groups and atoms. The molecules can be stabilized when it will remove eclipsing strain.

Answer 7

Chapter 4, Problem 29P

(a)

Interpretation Introduction

Interpretation : Puckered conformation of methylcyclobutane needs to be determined.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The eclipsing strain is due to the nonbonding interactions of the groups and atoms. The molecules can be stabilized when it will remove eclipsing strain.

Answer 8

(b)

Interpretation Introduction

Interpretation : Puckered conformation of cis-1, 2-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

Answer 9

(b)

Interpretation Introduction

Interpretation : Puckered conformation of cis-1, 2-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

Answer 10

(c)

Interpretation Introduction

Interpretation : Puckered conformation of trans-1, 2-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

Answer 11

(c)

Interpretation Introduction

Interpretation : Puckered conformation of trans-1, 2-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

Answer 12

(d)

Interpretation Introduction

Interpretation : Puckered conformation of cis-1, 3-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

Answer 13

(d)

Interpretation Introduction

Interpretation : Puckered conformation of cis-1, 3-dimethylcyclobutane needs to be drawn.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

Answer 14

(e)

Interpretation Introduction

Interpretation : Puckered conformation of trans-1, 3-dimethylcyclobutane needs to be drawn. Also, the stability of cis and trans 1,2dimethylcyclobutane and cis and trans 1,3dimethylcylobutane needs to be compared.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

The conformers have the same molecular formula, but the spacious arrangements of the groups are different.

Answer 15

(e)

Interpretation Introduction

Interpretation : Puckered conformation of trans-1, 3-dimethylcyclobutane needs to be drawn. Also, the stability of cis and trans 1,2dimethylcyclobutane and cis and trans 1,3dimethylcylobutane needs to be compared.

Concept Introduction : In cyclobutane, number of eclipsing strains is present. To remove these strains one carbon atom goes out of the plane and the molecules starts bending or puckering. The molecules can be stabilized when it will remove eclipsing strain.

The conformers have the same molecular formula, but the spacious arrangements of the groups are different.

Answer 16

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Ch. 4.1 - Prob. 4.1E Ch. 4.1 - Prob. 4.3TIY Ch. 4.2 - Prob. 4.4E Ch. 4.2 - Prob. 4.6TIY Ch. 4.3 - Prob. 4.7E Ch. 4.4 - Prob. 4.8E Ch. 4.4 - Prob. 4.10TIY Ch. 4.4 - Prob. 4.11E Ch. 4.4 - Prob. 4.12E Ch. 4.4 - Prob. 4.14TIY

Solution Summary: The author explains how the puckered conformation of methylcyclobutane needs to be determined.

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