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Chapter 9: Q52E (page 286)

1-Octen-3-ol, a potent mosquito attractant commonly used in mosquito traps, can be prepared in two steps from hexanal, CH3CH2CH2CH2CH2CHO . The first step is an acetylide-addition reaction like that described in Problem 9-50. What is the structure of the product from the first step, and how can it be converted into 1-octen-3-ol?

Short Answer

Expert verified

The structure of acetylide anion is -C鈮�CH.

When this acetylide anion is added to the carbonyl group then C=O鈫�C鈭�OH. The Carbonyl group gives a nucleophilic addition reaction. The acetylide anion adds to the carbonyl group.

Step by step solution

01

Addition of acetylide anion

The structure of acetylide anion is -C鈮�CH.

When this acetylide anion is added to the carbonyl group then C=O鈫�C鈭�OH. The Carbonyl group gives a nucleophilic addition reaction. The acetylide anion adds to the carbonyl group.

02

Mechanism of reaction

Hexanal is reacted with acetylide anion to give alkyne intermediate. Which on further reaction with 1 equivalent of H2gives 1-Octen-3-ol.

Mechanism of reaction

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Most popular questions from this chapter

The following cycloalkyne is too unstable to exist. Explain

How would you prepare the following carbonyl compounds starting from an alkyne (reddish brown Br)?

How would you carry out the following transformation? More than one

step is needed.

Show the terminal alkyne and alkyl halide from which the following products can be obtained. If two routes look feasible, list both.

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Muscalure
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