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Show how you would accomplish the following synthetic conversions

(a)

(b)

(c)

(d)

Short Answer

Expert verified

(a)

(b)

(c)

(d)

Step by step solution

01

(a): Synthetic compound

A compound is synthesized by a chemical reaction rather than arising naturally.These types of compounds have control by humans in any chemical reaction.

Phenol is a cyclic organic compound that contains one hydroxyl group.

02

Conversion

Phenol reacted with sodium forms an intermediate which in reaction with bromomethyl forms ethyl phenyl ether.

Formation of ethyl phenyl ether

03

(b) : Toluene

Toluene is an aromatic compound that contains a methyl group attached to the phenyl. It is colourless and used in oil refining, and paints.

04

Conversion

2 moles of Toluene-2-bromomethyl treated with sodium hydroxide forms respective alcohol. Then treated with 1 equivalent of sodium hypochlorite form aldehyde, then hydrolyzed and treated with sulfuric acid form 1-methyl-2-[2-(2-methylphenyl)ethyl]benzene.

Formation of 1-methyl-2-[2-(2-methylphenyl) ethyl] benzene

05

(c): Bromobenzene

Bromobenzene is an aromatic compound that is a colourless liquid and acts as a reagent. Bromine is attached to the benzene. Used as solvent.

06

Conversion

Bromobenzene was treated with bromo magnesio benzene, then treated with butan-1-al followed by hydrolysis from respective alcohol. Then finally treated with form cyclopentan-1-butanone.

Formation of cyclopentan-1-butanone

07

(d):Cyclohexan-1-methanol

Cyclohexan-1-methanol is an aromatic compound that contains a methyl alcohol group.

08

Conversion

Cyclohexan-1-methanol treated with 1 equivalent of form cyclohexan-1-al, which on further reaction with bromo magnesio ethyl form cyclohexan-1-propanol.

Formation of cyclohexan-1-propanol

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Most popular questions from this chapter

Neopentyl alcohol, (CH3)3CCH2OH, reacts with concentrated HBr to give 2-bromo-2-methylbutane, a rearranged product. Propose a mechanism for the formation of this product.

Predict the major products of dehydration catalyzed by sulfuric acid.

(a) heptan-1-ol

(b) heptan-2-ol

(c) pentan-2-ol

(d) 1-methylcyclohexanol

(e) Cyclohexylmethanol

(f) 2-methylcyclohexanol

Two products are observed in the following reaction.

(a) Suggest a mechanism to explain how these two products are formed.

(b) Your mechanism for part (a) should be different from the usual mechanism of the reaction of SOCl2 with alcohols. Explain why the reaction follows a different mechanism in

this case.

Predict the major products of the following reactions.

(a)ethyl tosylate+potassium tert-butoxide

(b) isobutyl tosylate + NaI

(c) (R)-2-hexyl tosylate + NaCN

(d) the tosylate of cyclohexylmethanol +excess NH3

A student wanted to use the Williamson ether synthesis to make (R)-2-ethoxybutane. He remembered that the Williamson synthesis involves an SN2 displacement, which takes place with inversion of configuration. He ordered a bottle of (S)-butan-2-ol for his chiral starting material. He also remembered that the SN2goes best on primary halides and tosylates, so he made ethyl tosylate and sodium (S)-but-2-oxide. After warming these reagents together, he obtained an excellent yield of 2-ethoxybutane.

(a) What enantiomer of 2-ethoxybutane did he obtain? Explain how this enantiomer results from the SN2 reaction of ethyl tosylate with sodium (S)-but-2-oxide.

(b) What would have been the best synthesis of (R)-2-ethoxybutane?

(c) How can this student convert the rest of his bottle of (S)-butan-2-ol to (R)-2-ethoxybutane?

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