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Chapter 20: 72P (page 1038)

Starting with benzene and any other reagents you need, show how you would synthesize the compound shown here. (Hint: Consider a Pd-catalyzed coupling for the final step).

Short Answer

Expert verified

In the presence of aluminum chloride, an acyl chloride reacts with benzene to give acetophenone. This reaction is known as Friedel crafts acylation reaction. Keto group is meta director so incoming electrophile attacks meta to keto group. The formed acetophenone undergoes chlorination (electrophilic substitution reaction) to give 3-chloroacetophenone.

Step by step solution

01

Formation of 3-chloro acetophenone

In the presence of aluminum chloride, an acyl chloride reacts with benzene to give acetophenone. This reaction is known as Friedel crafts acylation reaction. Keto group is meta director so incoming electrophile attacks meta to keto group. The formed acetophenone undergoes chlorination (electrophilic substitution reaction) to give 3-chloroacetophenone.

02

Formation of the desired product

The heck coupling reaction is a palladium-catalyzed cross-coupling reaction in which alkyl halide reacts with an alkene to give the substituted product in a basic medium. The compound,3-chloroacetophenone undergoes a heck coupling reaction with but-1-ene to give the desired product.

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Most popular questions from this chapter

Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.

(a)methyl salicylate

(b) methyl formate (32°C)

(c) ethyl phenylacetate

In the presence of a trace of acid, δ-hydroxyvaleric acid forms a cyclic ester (lactone).

HO-CH2CH2CH2CH2-COOH

δ-hydroxyvaleric acid

(a)Give the structure of the lactone, called δ-valerolactone.

(b) Propose a mechanism for the formation of δ-valerolactone.

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(a) isopentyl alcohol isopentyl acetate (banana oil)

(b) 3-ethylpentanoic acid3-ethylpentanenitrile

(c) isobutylamineN-isobutylformamide

(d) ethyl acetate3-methylpentan-3-ol

(e) cyclohexylamineN-cyclohexylacetamide

(f) bromocyclohexanedicyclohexylmethano

(g)

(h)

Show how you would synthesize the following compounds, starting with acetylene and any compounds containing no more than four carbon atoms.

(a)hex-1-yne

(b)hex-2-yne

(c)cis-hex-2-ene

(d)trans-hex-2-ene

(e)1,1-dibromohexane

(f)2,2-dibromohexane

(g)pentanal, CH3CH2CH2CH2CHO

(h)pentan-2-one, CH3-CO-CH 2CH2 CH3

(i) (+/)-3,4-dibromohexane

(j)meso-butan-2,3-diol

(k)2-methylhex-3-yn-2-ol

Show how you would synthesize 2-phenylhex-3-yn-2-ol, starting with acetophenone (PhCOCH3 ) and any other reagents you need. (“2-ol” means there is an OH group on C2.)
See all solutions

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