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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

Question: Fill in the boxes:

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

How would you make the following compounds from N-benzylbenzamide? a. dibenzylamine b. benzoic acid c. benzyl alcohol

Question: Fill in the boxes with the appropriate reagents:

a. Write the mechanism for the following reactions:

1. the acid-catalyzed hydrolysis of an imine to a carbonyl compound and a primary amine

2. the acid-catalyzed hydrolysis of an enamine to a carbonyl compound and a secondary amine

b. How do the two mechanisms differ?
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