Chapter 17, Problem 17.49P

Interpretation Introduction

(a)

Interpretation:

The detailed mechanism of the given reaction is to be drawn. Using the mechanism, the reaction product is to be predicted.

Concept introduction:

Alkyllithium ($\text{RLi}$) has a polar covalent $\text{C-Li}$ bond with a partial negative charge on the carbon. The alkyl group acts as a nucleophile as well as a base and can be treated as ${\text{:R}}^{-}$. This makes it useful for formation of new $\text{C-C}$ bond with a substrate that contains an electron-poor carbon. An aldehyde forms a secondary alcohol when treated with an alkyllithium reagent, and a ketone forms a tertiary alcohol.

Deuterium (D) is a heavy isotope of hydrogen and, in chemical reactions, behaves in much the same manner.

Interpretation Introduction

(b)

Interpretation:

The detailed mechanism of the given reaction is to be drawn. Using the mechanism, the reaction product is to be predicted.

Concept introduction:

Alkyllithium ($\text{RLi}$) has a polar covalent $\text{C-Li}$ bond with a partial negative charge on the carbon. The alkyl group acts as a nucleophile as well as a base and can be treated as ${\text{:R}}^{-}$. This makes it useful for formation of new $\text{C-C}$ bond with a substrate that contains an electron-poor carbon. An aldehyde forms a secondary alcohol when treated with an alkyllithium reagent, and a ketone forms a tertiary alcohol.

Deuterium (D) is a heavy isotope of hydrogen and, in chemical reactions, behaves in much the same manner.

Interpretation Introduction

(c)

Interpretation:

The detailed mechanism of the given reaction is to be drawn. Using the mechanism, the reaction product is to be predicted.

Concept introduction:

Alkyllithium ($\text{RLi}$) has a polar covalent $\text{C-Li}$ bond with a partial negative charge on the carbon. The alkyl group acts as a nucleophile as well as a base and can be treated as ${\text{:R}}^{-}$. This makes it useful for formation of new $\text{C-C}$ bond with a substrate that contains an electron-poor carbon. An aldehyde forms a secondary alcohol when treated with an alkyllithium reagent, and a ketone forms a tertiary alcohol.

Deuterium (D) is a heavy isotope of hydrogen and, in chemical reactions, behaves in much the same manner.