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Show how you would accomplish the following syntheses.

Chapter 15, Problem 54SP

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QUESTION:

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 acid -ethylpentanenitrile

(c) isobutylamine  -isobutylformamide

(d) ethyl acetate  3-methylpentan-3-ol

(e) cyclohexylamine  -cyclohexylacetamide

(f) bromocyclohexane  dicyclohexylmethanol




Questions & Answers

QUESTION:

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 acid -ethylpentanenitrile

(c) isobutylamine  -isobutylformamide

(d) ethyl acetate  3-methylpentan-3-ol

(e) cyclohexylamine  -cyclohexylacetamide

(f) bromocyclohexane  dicyclohexylmethanol




ANSWER:

Solution:

Here we have to show the following synthesis

Step 1

(a) isopentyl alcohol isopentyl acetate (banana oil)

Isopentyl alcohol in presence of acetic anhydride (CH3-CO-O-CO-CH3) release one molecule of acetic acid and forms methoxy-2-methylbutane.

+CH3COOH

(isopentyl alcohol )                 (isopentyl acetate)

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