Question

Using benzene and any necessary organic or inorganic reagents, suggest efficient syntheses of (a) Isobuty benzene, $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right)_{2}$ (b) (2,2-Dimethylpropyl)\mathrm{ benzene, } \mathrm { C } _ { 6 } \mathrm { H } _ { 5 } \mathrm { CH } _ { 2 } \mathrm { C } ( \mathrm { CH } _ { 3 } ) _ { 3 } Sample Solution (a) Friedel-Crafts alkylation of benzene with isobutyl chloride is not suitable, because it yields tert-butylbenzene by rearrangement (see $\underline{\text { Section } 13.6) .}$ The two-step acylation-reduction sequence is required. Acylation of benzene puts the side chain on the ring with the correct carbon skeleton. Next, Clemmensen reduction converts the carbonyl group to a methylene group.

          Using benzene and any necessary organic or inorganic reagents, suggest efficient syntheses of
(a) Isobuty benzene, $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right)_{2}$
(b) (2,2-Dimethylpropyl)\mathrm{ benzene, } \mathrm { C } _ { 6 } \mathrm { H } _ { 5 } \mathrm { CH } _ { 2 } \mathrm { C } ( \mathrm { CH } _ { 3 } ) _ { 3 }
Sample Solution (a) Friedel-Crafts alkylation of benzene with isobutyl chloride is not suitable, because it yields tert-butylbenzene by rearrangement (see $\underline{\text { Section } 13.6) .}$
The two-step acylation-reduction sequence is required. Acylation of benzene puts the side chain on the ring with the correct carbon skeleton. Next, Clemmensen reduction converts the carbonyl group to a methylene group.

Added by Elena B.

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