a) Interpretation: The product expected during hydration of 4-octyne is to be given. Concept introduction: Addition of water to triple bonds occurs following Markovnikov regiochemistry to yield an enol as the product. The enol tautomerizes to give a ketone as the final product. Terminal alkenes and symmetrically substituted internal alkynes yield only one product. Unsymmetrically substituted internal alkynes yield a mixture of ketones as product. To give: The product expected during hydration of 4-octyne.

Question

What products would you expect from reaction of the following alkenes with NBS? If more than one product is formed, show the structures of all.

Answer 1

Question

Chapter 9.4, Problem 4P

Interpretation Introduction

a)

Interpretation:

The product expected during hydration of 4-octyne is to be given.

Concept introduction:

Addition of water to triple bonds occurs following Markovnikov regiochemistry to yield an enol as the product. The enol tautomerizes to give a ketone as the final product. Terminal alkenes and symmetrically substituted internal alkynes yield only one product. Unsymmetrically substituted internal alkynes yield a mixture of ketones as product.

To give:

The product expected during hydration of 4-octyne.

b)

Interpretation Introduction

Interpretation:

The product expected during hydration of 2-methyl-4-octyne is to be given.

Concept introduction:

Addition of water to triple bonds occurs following Markovnikov regiochemistry to yield an enol as the product. The enol tautomerizes to give a ketone as the final product. Terminal alkenes and symmetrically substituted internal alkynes yield only one product. Unsymmetrically substituted internal alkynes yield a mixture of ketones as product.

To give:

The products expected during hydration of 2-methyl-4-octyne.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

What products would you expect from reaction of the following alkenes with NBS? If more than one product is formed, show the structures of all.

Show how could you prepare the following compounds starting from benzene:

Show how you would synthesize the following compounds from alkyl halides, vinylhalides, and aryl halides containing no more than six carbon atoms. vinylcyclohexane

Answer 2

Question

Chapter 9.4, Problem 4P

Interpretation Introduction

a)

Interpretation:

The product expected during hydration of 4-octyne is to be given.

Concept introduction:

Addition of water to triple bonds occurs following Markovnikov regiochemistry to yield an enol as the product. The enol tautomerizes to give a ketone as the final product. Terminal alkenes and symmetrically substituted internal alkynes yield only one product. Unsymmetrically substituted internal alkynes yield a mixture of ketones as product.

To give:

The product expected during hydration of 4-octyne.

b)

Interpretation Introduction

Interpretation:

The product expected during hydration of 2-methyl-4-octyne is to be given.

Concept introduction:

Addition of water to triple bonds occurs following Markovnikov regiochemistry to yield an enol as the product. The enol tautomerizes to give a ketone as the final product. Terminal alkenes and symmetrically substituted internal alkynes yield only one product. Unsymmetrically substituted internal alkynes yield a mixture of ketones as product.

To give:

The products expected during hydration of 2-methyl-4-octyne.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 3

Question

Chapter 9.4, Problem 4P

Interpretation Introduction

a)

Interpretation:

The product expected during hydration of 4-octyne is to be given.

Concept introduction:

Addition of water to triple bonds occurs following Markovnikov regiochemistry to yield an enol as the product. The enol tautomerizes to give a ketone as the final product. Terminal alkenes and symmetrically substituted internal alkynes yield only one product. Unsymmetrically substituted internal alkynes yield a mixture of ketones as product.

To give:

The product expected during hydration of 4-octyne.

b)

Interpretation Introduction

Interpretation:

The product expected during hydration of 2-methyl-4-octyne is to be given.

Concept introduction:

Addition of water to triple bonds occurs following Markovnikov regiochemistry to yield an enol as the product. The enol tautomerizes to give a ketone as the final product. Terminal alkenes and symmetrically substituted internal alkynes yield only one product. Unsymmetrically substituted internal alkynes yield a mixture of ketones as product.

To give:

The products expected during hydration of 2-methyl-4-octyne.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 4

Question

Chapter 9.4, Problem 4P

Interpretation Introduction

a)

Interpretation:

The product expected during hydration of 4-octyne is to be given.

Concept introduction:

Addition of water to triple bonds occurs following Markovnikov regiochemistry to yield an enol as the product. The enol tautomerizes to give a ketone as the final product. Terminal alkenes and symmetrically substituted internal alkynes yield only one product. Unsymmetrically substituted internal alkynes yield a mixture of ketones as product.

To give:

The product expected during hydration of 4-octyne.

b)

Interpretation Introduction

Interpretation:

The product expected during hydration of 2-methyl-4-octyne is to be given.

Concept introduction:

Addition of water to triple bonds occurs following Markovnikov regiochemistry to yield an enol as the product. The enol tautomerizes to give a ketone as the final product. Terminal alkenes and symmetrically substituted internal alkynes yield only one product. Unsymmetrically substituted internal alkynes yield a mixture of ketones as product.

To give:

The products expected during hydration of 2-methyl-4-octyne.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 5

Chapter 9.4, Problem 4P

Interpretation Introduction

a)

Interpretation:

The product expected during hydration of 4-octyne is to be given.

Concept introduction:

Addition of water to triple bonds occurs following Markovnikov regiochemistry to yield an enol as the product. The enol tautomerizes to give a ketone as the final product. Terminal alkenes and symmetrically substituted internal alkynes yield only one product. Unsymmetrically substituted internal alkynes yield a mixture of ketones as product.

To give:

The product expected during hydration of 4-octyne.

b)

Interpretation Introduction

Interpretation:

The product expected during hydration of 2-methyl-4-octyne is to be given.

Concept introduction:

Addition of water to triple bonds occurs following Markovnikov regiochemistry to yield an enol as the product. The enol tautomerizes to give a ketone as the final product. Terminal alkenes and symmetrically substituted internal alkynes yield only one product. Unsymmetrically substituted internal alkynes yield a mixture of ketones as product.

To give:

The products expected during hydration of 2-methyl-4-octyne.

Answer 6

Chapter 9.4, Problem 4P

Interpretation Introduction

a)

Interpretation:

The product expected during hydration of 4-octyne is to be given.

Concept introduction:

Addition of water to triple bonds occurs following Markovnikov regiochemistry to yield an enol as the product. The enol tautomerizes to give a ketone as the final product. Terminal alkenes and symmetrically substituted internal alkynes yield only one product. Unsymmetrically substituted internal alkynes yield a mixture of ketones as product.

To give:

The product expected during hydration of 4-octyne.

Answer 7

Chapter 9.4, Problem 4P

Interpretation Introduction

a)

Interpretation:

The product expected during hydration of 4-octyne is to be given.

Concept introduction:

Addition of water to triple bonds occurs following Markovnikov regiochemistry to yield an enol as the product. The enol tautomerizes to give a ketone as the final product. Terminal alkenes and symmetrically substituted internal alkynes yield only one product. Unsymmetrically substituted internal alkynes yield a mixture of ketones as product.

To give:

The product expected during hydration of 4-octyne.

Answer 8

b)

Interpretation Introduction

Interpretation:

The product expected during hydration of 2-methyl-4-octyne is to be given.

Concept introduction:

Addition of water to triple bonds occurs following Markovnikov regiochemistry to yield an enol as the product. The enol tautomerizes to give a ketone as the final product. Terminal alkenes and symmetrically substituted internal alkynes yield only one product. Unsymmetrically substituted internal alkynes yield a mixture of ketones as product.

To give:

The products expected during hydration of 2-methyl-4-octyne.

Answer 9

b)

Interpretation Introduction

Interpretation:

The product expected during hydration of 2-methyl-4-octyne is to be given.

Concept introduction:

Addition of water to triple bonds occurs following Markovnikov regiochemistry to yield an enol as the product. The enol tautomerizes to give a ketone as the final product. Terminal alkenes and symmetrically substituted internal alkynes yield only one product. Unsymmetrically substituted internal alkynes yield a mixture of ketones as product.

To give:

The products expected during hydration of 2-methyl-4-octyne.

Answer 10

Expert Solution & Answer

Answer 11

Expert Solution & Answer

Answer 12

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 13

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 14

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 15

Trending nowThis is a popular solution!

Answer 16

Trending nowThis is a popular solution!

Answer 17

Trending nowThis is a popular solution!

Answer 18

Trending now

Answer 19

This is a popular solution!

Answer 20

See solution

Check out sample textbook solution

Answer 21

Ch. 9.1 - Prob. 1P Ch. 9.1 - Prob. 2P Ch. 9.3 - What products would you expect from the following...Ch. 9.4 - Prob. 4P Ch. 9.4 - Prob. 5P Ch. 9.4 - Prob. 6P Ch. 9.4 - Prob. 7P Ch. 9.5 - Using any alkyne needed, how would you prepare the...Ch. 9.7 - The pKa of acetone, CH3COCH3, is 19.3. Which of...Ch. 9.8 - Prob. 10P

Concept explainers

Chapter 9 Solutions