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Chapter 20: Q19 Pb (page 1066)

Show how you would synthesize the following compounds from the appropriate carboxylic acids or acid derivatives.

a)


b)



c)

Short Answer

Expert verified

a)


b)

c)

Step by step solution

01

Carboxylic acids or acid derivatives 

Carboxylic acids are the COOH- containing compounds, and acid derivatives are the compounds formed when the OH group of a carboxylic acid is replaced by Cl (acid chloride) or - NH2(amide). There are three types of acid derivatives: acid halides, esters, and amides.

02

Synthesis of phenylacetic acid 

(a) Isopropyl alcohol is synthesized when phenylacetic acid is treated with LiAlH4 and further with H3O+. Another method is by treating phenylacetic acid with B2H6 and then with H3O+.


Synthesis of phenylacetic acid

03

Synthesis of phenylacetaldehyde 

Phenylacetaldehyde is synthesized when phenylacetyl chloride is treated with LiAIH(O - t - Bu)3and further with H3O+ .

04

Formation of phenylacetaldehyde 

Synthesis of phenylacetaldehyde

05

Synthesis of compounds 

The COOH group of a reactant is converted to CH2OH-when the reactant is treated with B2H6 and further with H3O+ .

06

Formation of compounds 

Synthesis of alcoholic compounds

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Most popular questions from this chapter

Show how the following ketones might be synthesized from the indicated acids, using any necessary reagents.

(a) propiophenone from propionic acid (two ways, using alkylation of the acid and using Friedel-Crafts acylation)

(b) methyl cyclohexyl ketone from cyclohexanecarboxylic acid

Predict the products of the following reactions.

(a)

(b)

(c)

(d)

(e)

(f)

product from part (e)

(g)

4-methylpentaoic acid

(h)

product from part (g)

Question: Name the following carboxylic acids (when possible, give both a common name and a systematic name).

(a)

(b)

(c)

(d)

(e)

(f)

Grignard reagents add to carbonate esters as they add to other esters.

(a) Predict the major product of the following reaction.

(b) Show how you would synthesize 3-ethylpentan-3-ol using diethyl carbonate and ethyl bromide as your only organic reagents.

(c) Diethyl carbonate is a liquid reagent that is easy to handle. In contrast, phosgene is a highly toxic and corrosive gas. Show how you might use diethyl carbonate instead of phosgene to make Lexan®. Also, show how you might use diethyl carbonate instead of methyl isocyanate to make Sevin® insecticide.

Question: Show how you would synthesize the following carboxylic acids, using the indicated starting materials.

(a) hex-3-yne→propanoicacid

(b) cis-cyclodecene→decanedioicacid

(c ) iodobenzene→phenylaceticacid

(d)pentan-3-ol→2-ethylbutanoicacid

(e)o-xylene→phthalicacid

(f) allylbromide→but-3-enoicacid
See all solutions

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