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Chapter 17: Q62P (page 848)

Show how the following compound can be synthesized from the given starting material.

Short Answer

Expert verified

The answer is,

Reaction mechanism

Step by step solution

01

Explanation

The reaction of acids on alcohol gives an alkene on undergoing dehydration reaction. And the reaction of ketone with strong bases like LDA, Lithium di-isopropyl amine to produce an enolate ion which undergoes reaction to give claisen condensation product.

02

Explanation

The reaction for the synthesis of the given compound is as shown below.

Reaction Mechanism

The reaction starts with the sulphuric acid reagent. The water molecule is eliminated from the compound giving an alkene.It is the treated with LDA in THF and 2-pentanone giving the product by condensation reaction.

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Most popular questions from this chapter

Problem: starting with bromocyclohexane, how can each of the following compounds be prepared?

The 1 H NMR chemical shifts of nitromethane, dinitromethane, and trinitromethane are at d 6.10, d 4.33, and d 7.52. Match each chemical shift with the compound. Explain how chemical shift correlates with pKa.

What two carbonyl compounds are required for the synthesis of morachalcone A (the aromatase inhibitor discussed in the box below), via a Claisen鈥揝chmidt condensation?

Which of the following compounds decarboxylates when heated?

a. What carboxylic acid is formed when the malonic ester synthesis is carried out with one equivalent of malonic ester, one equivalent of 1,5-dibromopentane, and two equivalents of base?

b. What carboxylic acid is formed when the malonic ester synthesis is carried out with two equivalents of malonic ester, one equivalent of 1,5-dibromopentane, and two equivalents of base?
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