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Chapter 16: Q19P (page 752)

Question: Show two ways to convert an alkyl halide into a carboxylic acid that has one more carbon than the alkyl halide.

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01

Reaction of the Grignard reagent with carbon dioxide (1)

The reaction ofhaloalkane with magnesium in the presence of diethyl ether converts into a Grignard reagent. Further reaction with carbon dioxide after hydrolysis gives a carboxylic acidwithone more carbon than the reactant.

The reaction is as follows.

Synthesis of carboxylic acid (1)

02

Reaction with cyanide (2)

When a haloalkane reacts with cyanide, itconverts the haloalkane into alkyl cyanide.On further reaction, hydrochloric acid and hydrolysis give carboxylic acid with one more carbon.

The reaction is as follows.

Synthesis of carboxylic acid (2)

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Most popular questions from this chapter

Hydration of an aldehyde is also catalyzed by hydroxide ion. Propose a mechanism for the reaction.

Rank the following compounds from most reactive to least reactive towards nucleophilic addition.

Rank the following compounds from most reactive to least reactive toward nucleophilic addition:

What is the product of each of the following reactions?

A compound gives the following IR spectrum. Upon reaction with sodium borohydride followed by acidification, it forms the product with the H1NMR spectrum shown below. Identify the starting material and the product.
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