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Chapter 20: Q21E (page 678)

Predict the product and provide the mechanism for each reaction below.

Short Answer

Expert verified

The product prediction and its mechanism for each of the reaction can be explained.

Step by step solution

01

Production prediction and mechanism for (a)

When bromobenzene treated with Mg in dry can yield the phenylmagnesium bromide. But treated with CO2, will add nucleophile of Grignard reagent to carbonyl carbon. It leads to the production of intermediate compound on hydrolysis with aqueous acid. The product is Benzoic acid.

The formation mechanism can be denoted as,

02

Production prediction and mechanism for (b)

When 2-bromobutane treated with Mg in dry can yield the 2-butylmagnesium bromide. But treated with CO2, will add nucleophile of Grignard reagent to carbonyl carbon. It leads to the production of intermediate compound on hydrolysis with aqueous acid. The product isButanoic acid.

The formation mechanism can be denoted as,

03

Production prediction and mechanism for (c)

When bromocyclopropane treated with Mg in dry can yield the propylmagnesium bromide. But treated with CO2, will add nucleophile of Grignard reagent to carbonyl carbon. It leads to the production of intermediate compound on hydrolysis with aqueous acid. The product is Cyclopropanecarboxylic acid.

The formation mechanism can be denoted as,

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Most popular questions from this chapter

Show how you might prepare the anti-inflammatory agent ibuprofen starting from isobutyl benzene. More than one step is needed.

Acid-catalyzed hydrolysis of a nitrile to give a carboxylic acid occursby initial protonation of the nitrogen atom, followed by nucleophilicaddition of water. Review the mechanism of base-catalyzed nitrilehydrolysis in Section 20-7 and then predict the products for each reaction below and write all of the steps involved in the acid-catalyzedreaction, using curved arrows to represent electron flow in each step.

What spectroscopic method could you use to distinguish among the following three isomeric acids? Tell what characteristic features you would expect for each acid

a) CH3(CH2)3CO2H - Pentanoic acid

b) (CH3)2CHCH2CO2H- 3-Methylbutanoic acid

c) (CH3)3CCO2H -2,2-Dimethylpropanoic acid

How would you carry out the following transformations? More than one step is needed in each case.

Thioglycolic acid, HSCH2CO2H, a substance used in depilatory agents
(hair removers) haspKa=3.42. What is the percent dissociation of
thioglycolic acid in a buffer solution at pH=3.0?
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