Chapter 10, Problem 29P

Interpretation Introduction

Interpretation:

Each of the given compoundsis to be synthesized from $\text{isopropyl alcohol}$.

Concept Introduction:

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The alcohol, in an acidic condition, undergoes dehydration by loss of ${\text{H}}_{\text{2}}\text{O}$ molecule and forms the corresponding alkene.

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The alkynes, on hydrogenation with the catalyst Lindlar palladium, form a cis alkene.

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The conjugate base of alkyne acts as a good nucleophile, and on reaction with a primary alkyl halide, undergoes a substitution reaction.

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The alkyne, on hydrogenation by a Group 1 metal (lithium, sodium, or potassium) in liquid ammonia, undergoes trans addition of ${\text{H}}_{\text{2}}$ and yields a trans alkene.

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The alkene, on reaction with hydrogen bromide in the presence of peroxide, undergoes an addition reaction in a way that hydrogen bonds to a more substituted carbon of double bond and bromine bonds to a less substituted carbon of double bond.This is called anti-Markovnikov's rule.

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Alkyne, on halogenation, forms vicinal dihalides.

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The primary alkyl halide on reaction with potassium cyanide undergoes substitution reaction and forms the corresponding alkyl nitrile.