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Chapter 21: 32P (page 817)

Draw the products of each reaction.

a.

b.

Short Answer

Expert verified

a.

b.

Step by step solution

01

Acetal Hydrolysis

Acetal is hydrolyzed via two-step mechanism, the acetal is converted to a hemiacetal and later into a carbonyl compound.

02

Consider the hydrolysis of the given acetals

a. The open acetal is converted to a hemiacetal by the nucleophilic addition of a water molecule and removal of one molecule of methanol. Later another molecule of methanol is removed forming the C-O bond. Deprotonation of the resonance stabilized carbocation would give the required carbonyl compound.


Formation of products in reaction a

b. The cyclic acetal undergoes nucleophilic attack by the water molecule in the acidic medium to form the corresponding gem-1,2-diol and carbonyl compound.

Formation of Products in reaction b

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Most popular questions from this chapter

What lactol (cyclic hemiacetal) is formed from intramolecular cyclization of each hydroxy aldehyde?

a.

b.

Devise a synthesis of each compound from cyclohexene and organic alcohols. You may use any other required organic or inorganic reagents

a)

b)

Rank the following compounds in order of increasing reactivity towards nucleophilic attack.

Give the IUPAC name for each aldehyde.

a.2-isobutyl-3-isopropylhexanal

b. trans-3-methylcyclopentanecarbaldehyde

c. 1-methylcyclopropanecarbaldehyde

d. 3,6-diethylnonanal

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.
See all solutions

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