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.