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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 cyanohydrin and carbonyl compound are formed when amygdalin is metabolized in a similar manner to linamarin?

Which compound in each pair forms the higher percentage of gem-diol at equilibrium?

a.

or

b.

or

Hydroxy aldehydes A and B readily cyclize to form hemiacetals. Draw the stereoisomersformed in this reaction from both A and B. Explain why this process gives an opticallyinactive product mixture from A, and an optically active product mixture from B.

Draw a stepwise mechanism for the following reaction, a key step in the synthesis of conivaptan (trade name Vaprisol), a drug used in the treatment of low sodium levels.

Maltose is a carbohydrate present in malt, the liquid obtained from barley and other grains. Although maltose has numerous functional groups, its reactions are explained by the same principles we have already encountered.

a. Label the acetal and hemiacetal carbons.b. What products are formed when maltose is treated with each of the following reagents: [1] ; [2] and HCl; [3] excess NaH, then excess ?c. Draw the products formed when the compound formed in Reaction [3] of part (b) is treated with aqueous acid.The reactions in parts (b) and (c) are used to determine structural features of carbohydrates like maltose. We will learn much more about maltose and similar carbohydrates in Chapter 28.
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