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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

An unknown compound C of molecular formula C6H12O3 exhibits a strong absorption in its IR spectrum at 1718 cm-1 and the given 1H NMR spectrum. What is the structure of C?

Draw a stepwise mechanism for the following reaction

Give the IUPAC name for each aldehyde.

a.2-isobutyl-3-isopropylhexanal

b. trans-3-methylcyclopentanecarbaldehyde

c. 1-methylcyclopropanecarbaldehyde

d. 3,6-diethylnonanal

What hydrolysis products are formed when the following compound is treated with aqueous acid?

Give the IUPAC name for each compound.

a.

b.

c.

d.

e.

f.
See all solutions

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