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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

What products are formed when each acetal is hydrolyzed with aqueous acid?

a.

b.

What reagents are needed to convert each compound into butanal (CH3CH2CH2CHO )?

a.

b.

c.

Rank the following compounds in order of increasing reactivity in nucleophilic addition

Show two methods to synthesize each alkene: a one-step method using a Wittig reagent, and a two-step method that forms a carbon–carbon bond with an organometallic reagent in one of the steps.

a.

b.

Two naturally occurring compounds that contain stable cyclic hemiacetals and acetals are monensin and digoxin, the chapter-opening molecule. Monensin, a polyether antibiotic produced by Streptomyces cinamonensis,is used as an additive in cattle feed. Digoxin is a widely prescribedcardiac drug used to increase the force of heart contractions. Label each acetal, hemiacetal, and ether in both compounds.
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