Question: Outline an efficient synthesis of each of the following compounds from the indicated starting material and any necessary organic or inorganic reagents: (a) Cyclopentyl cyanide

Outline an efficient synthesis of each of the following compounds from the indicated starting material and any necessary organic or inorganic reagents:
(a) Cyclopentyl cyanide from cyclopentane
(b) Cyclopentyl cyanide from cyclopentene
(c) Cyclopentyl cyanide from cyclopentanol
(d) NCCH2CH2CN from ethyl alcohol
(e) Isobutyl iodide from isobutyl chloride
(f) Isobutyl iodide from tert-butyl chloride
(g) Isopropyl azide from isopropyl alcohol
(h) Isopropyl azide from 1-propanol
(i) (S)-sec-Butyl azide from (R)-sec-butyl alcohol
(j) (S)-CH3CH2CHCH3 from (R)-sec-butyl alcohol

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a Cyclopentyl cyanide can be prepared from a cyclopentyl halide by a nucleophilic substitution reaction The first task therefore is to convert cyclopentane to a cyclopentyl halide light or heat Cyclop... View full answer

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