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Chapter 20: Q74 (page 815)

Draw a stepwise mechanism for the following reaction.

Short Answer

Expert verified

The alkyl group in alkyl lithium (an organometallic reagent) bears a negative charge (i.e., it acts as a carbanion) due to the high electropositivity of lithium.

Step by step solution

01

Alkyl lithium

The alkyl group in alkyl lithium (an organometallic reagent) bears a negative charge (i.e., it acts as a carbanion) due to the high electropositivity of lithium.

02

Reaction of carbonyl compounds with alkyl lithium

A general reaction between a carbonyl compound and an alkyl lithium reagent is shown below.

The reaction of ketone with RLi

03

Mechanism

The mechanism of the given reaction is shown below.

Mechanism

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Most popular questions from this chapter

Reaction of benzyl magnesium chloride with formaldehyde yields alcohols N and P after protonation. Draw a stepwise mechanism that shows how both products are formed.

Design a synthesis of each compound from alcohols having four carbons or fewer as the only organic starting materials. You may use any other inorganic reagents you choose.

Propose two different methods to synthesize oct-1-en-3-ol [CH3CH24CHOHCH=CH2] using a Grignard reagent and a carbonyl compound. Oct-1-en-3-ol is commonly called matsutake alcohol because it was first isolated from the Japanese matsutake mushroom.

Explain why the ฮฒ carbon of an ,ฮฑ,ฮฒ-unsaturated carbonyl compound absorbs farther downfield in the C13NMR spectrum than the a carbon, even though the ฮฑcarbon is closer to the electron-withdrawing carbonyl group. For example, the ฮฒ carbon of mesityl oxide absorbs at 150.5 ppm, while the carbon absorbs at 122.5 ppm.

Design a synthesis of (R)-salmeterol (Figure 20.3) from the following starting materials.
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