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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

:(a) Give the IUPAC name for A and B. (b) Draw the product formed when A or B is treated with each reagent: [1] NaBH4 [2] CH3MgBr then H2O ; [3] Ph3P=CHOCH3 ;[4] CH3CH2CH2NH2mild acid; [5] HOCH2CH2CH2OH,H+ .

Consider the para-substituted aromatic ketones, NO2C6H4COCH2 (p-nitroacetophenone) and CH3OC6H4COCH3 (p-methoxyacetophenone).

a. Which carbonyl compound is more stable?

b. Which compound forms the higher percentage of hydrate at equilibrium?

c. Which compound exhibits a carbonyl absorption at a higher wavenumber in its IR spectrum?

Explain your reasoning in each part.

Draw the products of each reaction.

a.

b.

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

a.

b.

c.

Give the IUPAC name for each ketone

a.

b

c
See all solutions

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