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Chapter 21: 72P (page 817)

Reaction of 5,5-dimethoxypentan-2-one with methylmagnesium iodide followed by treatment with aqueous acid forms cyclic hemiacetal Y. Draw a stepwise mechanism that illustrates how Y is formed

Short Answer

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Mechanism

Step by step solution

01

Grignard reagents reaction

The Grignard reagent acts as a nucleophile and attacks the carbonyl carbon to produce the corresponding alcoholic product.

Acetals undergo hydrolysis in presence of an acidic medium and undergo deprotection.

02

Stepwise mechanism

The Grignard reagent CH3Mgl adds to the carbonyl yielding the corresponding tertiary alcohol after protonation Deprotection of acetals occur in the presence of acid to yield the corresponding aldehyde Intramolecular cyclization occurs which produces the required product.

Mechanism

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Most popular questions from this chapter

The boiling point of butan-2-one ( 79.64oC ) is significantly higher than the boiling point of diethyl ether ( 34.6OC), even though both compounds exhibit dipole–dipole interactions and have comparable molecular weights. Offer an explanation.

Show two different methods to carry out the following transformation: a one-step method using a Wittig reagent, and a two-step method using a Grignard reagent. Which route, if any, is preferred?

Draw the products of each reaction.

a.

b.

Draw the products of the following Wittig reactions

a.

b.

Identify the acetal in oleandrin, and draw the products formed by acid-catalysed hydrolysis of the acetal.
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