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

Draw the major product of the following E2 reaction. Make sure you pay attention to REGIOCHEMISTRY and STEREOCHEMISTRY. Explain why this product is formed using 10 words or less for each. (a) NaH Br acetone TSO, NaH (b) acetone

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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Draw the major product of the following E2 reaction. Make sure you pay attention to REGIOCHEMISTRY and STEREOCHEMISTRY. Explain why this product is formed using 10 words or less for each. (a) NaH Br acetone TSO, NaH (b) acetone

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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.

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Answer 27

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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