Interpretation:
Thegiven compounds are to be prepared by using the toluene, sodium cyanide, and carbon dioxide as the sources of the carbon atoms, along with any necessary inorganic reagents.
Concept introduction:
The oxidation of alkyl benzene using strong oxidizing agent
The hydroxyl group of carboxylic acid can be substituted with chlorine atom by reaction with thionyl chloride to form acyl chloride.
The condensation of alcohol with carboxylic acid forms an ester.
The primary amide can be prepared by the acylation of ammonia.
Electron donating groups activates the arenes and gives electrophilic substitution at ortho-para position.
Electron withdrawing groups deactivates the arenes and gives electrophilic substitution at meta position.
The treatment of Grignard’s reagent on carbon dioxide forms a carboxylic acid.
The alkyl cyanide (nitrile) on hydrolysis yields carboxylic acid.
Alkyl cyanide (nitrile) can be prepared by the nucleophilic substitution of
Aryl cyanide can be synthesized by using a Sandmeyer reaction where, the aryl diazonium salt is treated with
The aryl diazonium salt is a key intermediate in synthesis of
The aryl chlorides can be converted to acid anhydride by nucleophilic acyl substitution using carboxylic acid.
The nitration is the electrophilic substitution of aromatic compound using reagent nitric acid in concentrated sulfuric acid
The nitrobenzene on reduction with
The benzylic bromide can be synthesized from toluene using
The benzoic acid on heating with calcium oxide reduced to benzene.
Answer to Problem 37P
Solution:
a)
b)
c)
d)
e)
f)
g)
h)
i)
Explanation of Solution
a) Benzoyl chloride
The benzoyl chloride can be synthesized starting with toluene.
The reaction sequence is shown below:
The toluene is oxidized to benzoic acid using a strong oxidizing agent
b) Benzoic anhydride
The reaction sequence for the synthesis of Benzoic anhydride is shown below:
The toluene is first converted to benzoic acid using strong oxidizing agent
c) Benzyl benzoate
The reaction sequence for the synthesis of benzyl benzoate is shown below:
The benzyl benzoate is an ester prepared by reacting the benzyl alcohol and benzoic acid. The benzoic acid is prepared by oxidizing toluene by using strong oxidizing agent
d) Benzamide
The benzamide is synthesized by the reaction of benzoyl chloride with ammonia. The benzoyl chloride is prepared by starting with toluene. The toluene is first converted to benzoic acid using strong oxidizing agent
The reaction sequence for the synthesis of benzamide is shown below:
e) Benzonitrile
In the first step, the toluene is converted to benzoic acid using a strong oxidizing agent
The reaction sequence for the synthesis of benzonitrile is shown below:
f) Benzyl cyanide
The reaction sequence for the synthesis of benzyl cyanide is shown below:
In the first step, the toluene is converted to benzyl bromide using a reagent
g) Phenylacetic acid
The reaction sequence for the synthesis of phenylacetic acid is shown below:
In the first step, the toluene is converted to benzyl bromide using a reagent
h)
The reaction sequence for the synthesis of
The toluene on nitration gave the mixture of ortho-nitro toluene and para-nitro toluene. The para-nitro toluene is then oxidized using a strong oxidizing agent
i)
The reaction sequence for the synthesis of
In first step, the toluene is oxidized to benzoic acid using a strong oxidizing agent
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Chapter 20 Solutions
Organic Chemistry - Standalone book
- Show how to prepare the following aromatic amines by aromatic nitration, followed by reduction. You may use benzene andtoluene as your aromatic starting materials. (c) m-bromoaniline (d) m-aminobenzoic acidarrow_forwardHow could you convert butanenitrile into the following compounds? Write each step showing the reagents needed. (a) 1-Butanol (b) Butylaminearrow_forwardShow how to synthesize the following amines from the indicated starting materials.(a) N-cyclopentylaniline from anilinearrow_forward
- Write a balanced chemical equation for each of the following reactions: (a) Phenol + sodium hydroxide (b) Product of part (a) + ethyl bromide (c) Product of part (a) + butyl p-toluenesulfonate (d) Product of part (a) + acetic anhydride (e) o-Cresol + benzoyl chloride (f) m-Cresol + ethylene oxide (g) 2,6-Dichlorophenol + bromine (h) p-Cresol + excess aqueous bromine (i) Isopropyl phenyl ether + excess hydrogen bromide + heatarrow_forwardDraw a structural formula for each amine and amine derivative. (a) N,N-Dimethylaniline (b) Triethylamine (c) tert-Butylamine (d) 1,4-Benzenediamine (e) 4-Aminobutanoic acid (f) (R)-2-Butanamine (g) Benzylamine (h) trans-2-Aminocyclohexanol (i) 1-Phenyl-2-propanamine (amphetamine) (j) Lithium diisopropylamide (LDA) (k) Benzyltrimethylammonium hydroxide (Triton B)arrow_forwardReaction of p-nitroaniline with sodium nitrite and hydrochloric acid at 0°C, followed by treatment with N,N-diethylaniline.arrow_forward
- Which, if any, of the following compounds can be prepared by a malonic ester synthesis? Show the alkyl halide you would use in each case. (a) Ethyl pentanoate (c) Ethyl 2-rnethylbutanoate (d) Ethyl 2,2-dimethylpropanoate (b) Ethyl 3-methylbutanoatearrow_forwardWrite a structural formula for each of the following compounds: (a) m-Chlorobenzoyl chloride (b) Trifluoroacetic anhydride (c) cis-1,2-Cyclopropanedicarboxylic anhydride (d) Ethyl cycloheptanecarboxylate (e) 1-Phenylethyl acetate (f) 2-Phenylethyl acetate (g) p-Ethylbenzamide (h) N-Ethylbenzamide (i) 2-Methylhexanenitrilearrow_forwardDraw the structure of each compound.(a) o-nitroanisole (b) 2,4-dimethoxyphenol (c) p-aminobenzoic acid(d) 4-nitroaniline (e) m-chlorotoluene (f) p-divinylbenzene(g) p-bromostyrene (h) 3,5-dimethoxybenzaldehyde (i) tropylium chloride(j) sodium cyclopentadienide (k) 2-phenylpropan-1-ol (l) benzyl methyl ether(m) p-toluenesulfonic acid (n) o-xylene (o) 3-benzylpyridinarrow_forward
- Show how you would synthesize each compound, starting with an ester containing nomore than eight carbon atoms. Any other necessary reagents may be used.(a) Ph3C¬OH (b) (PhCH2)2CHOHarrow_forwardHow could you convert butanenitrile into the following compounds? Write each step showing the reagents needed.(a) 1-Butanol(b) Butylamine(c) 2-Methyl-3-hexanonearrow_forwardShow how you might utilize the reduction of an amide, oxime, or a nitrile to carry out each of the following transformations (a)Benzoic acid to N-ethyl-N-benzylamine (b)1-Bromopentane to hexylamine (c)Propanoic acid to tripropylamine (d)2-Butanone to sec-butylaminearrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning