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Chapter 22: Q42E (page 752)

Predict the product(s) of the following reactions:

Short Answer

Expert verified

Chemical reaction (a)

Chemical reaction (b)

Chemical reaction (c)

Chemical reaction (d)

Step by step solution

01

The product of reaction (a)

The product formed from the given reaction is,

Chemical reaction (a)

One of the carboxylic acid group is removed from the gem di carboxylate group and forms a monocarboxylic acid group.

02

The product of reaction (b)

The product formed from the given reaction is,

Chemical reaction (b)

The -CH2group that is in between the two electron withdrawing groups will be the most acidic group and on reaction with a base, it forms a carbanion intermediate.

This on reaction with alkyl halide, forms a new C-C bond.

03

The product of reaction (c)

The product formed from the given reaction is,

Chemical reaction (c)

04

The product of reaction (d)

The product formed from the given reaction is,

Chemical reaction (d)

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Most popular questions from this chapter

When a ketone is treated with acid and a halogen, the a-monohalogenated product can be obtained in high yield. However, under basic conditions it is extremely difficult to isolate the mono halogenated product. Provide an explanation for this reactivity.

Heating carvone with aqueous sulfuric acid converts it into carvacrol. Propose a mechanism for the isomerization.

Draw structures for the enol tautomers of the following compounds:

(a) Cyclopentanone

(b) Methyl thioacetate

(c) Ethyl acetate

(d) Propanal

(e) Acetic acid

(f) Phenylacetone

All attempts to isolate primary and secondary nitroso compounds result solely in the formation of oximes. Tertiary nitroso compounds, however, are stable. Explain.


The two optically beta-keto acids below were decarboxylated using the conditions typically used for the acetoacetate synthesis. Will the ketone products also be optically active? Provide the complete mechanism to explain your answer.
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