Chapter 21, Problem 21.51P

(a)

Interpretation Introduction

Interpretation:

Synthesis of benzoic acid has to be shown.

Concept Introduction:

Benzoic acid can be synthesized from ethyl benzene using $KMn{O}_4$ in acidic medium and at optimum temperature. The reagent acts as a strong oxidizing agent.

(b)

Interpretation Introduction

Interpretation:

Synthesis of 1-bromo-1-phenylethane has to be shown.

Concept Introduction:

1-bromo-1-phenylethane can be synthesized using the reagents $NBS,{\left(PhC{O}_2\right)}_{2}andCC{l}_4.$ This reagents is used for allylic bromination.

(c)

Interpretation Introduction

Interpretation:

Synthesis of styrene has to be shown.

Concept Introduction:

The reagent used for the conversion of 1-bromo-1-phenylethane to styrene is $tert-Bu{O}^{-}$, the product is formed through elimination reaction.

(d)

Interpretation Introduction

Interpretation:

Synthesis of 1-phenylethanol has to be shown.

Concept Introduction:

1-phenyl ethanol can be synthesized from styrene by the addition of water in acidic medium.

(e)

Interpretation Introduction

Interpretation:

Synthesis of acetophenone has to be shown.

Concept Introduction:

Acetophenone can be synthesized from benzene and benzene can be synthesized from benzoic acid.  When $C{H}_{3}COCl,AlC{l}_3$ treated with benzene electrophilic substitution reaction occurs and acetophenone will be formed.

(f)

Interpretation Introduction

Interpretation:

Synthesis of 2-phenylethanol has to be shown.

Concept Introduction:

2-phenylethanol can be synthesized from styrene through hydroboration oxidation reaction.

(g)

Interpretation Introduction

Interpretation:

Synthesis of phenyl acetaldehyde has to be shown.

Concept Introduction:

phenyl acetaldehyde can be synthesized from styrene.

The reagent titanosilicate and hydrogen peroxide enhance the ethylene epoxidation reaction.

Al-SBA-15 is an aluminosilicate compound having mesoporous structure. It helps in isomerization of epoxide.

(h)

Interpretation Introduction

Interpretation:

Synthesis of 2-phenylacetic acid has to be shown.

Concept Introduction:

The ester formed during this reaction is treated with $\text{NaOH}$ in order to get carboxylic acid containing product.

(i)

Interpretation Introduction

Interpretation:

Synthesis of 1,2-dibromo-1-phenylethane has to be shown.

Concept Introduction:

1,2-dibromo-1-phenylethane can be synthesized from styrene through bromination reaction.

(j)

Interpretation Introduction

Interpretation:

Synthesis of phenylethyne has to be shown.

Concept Introduction:

phenylethyne can be synthesized from 1,2-dibromo-1-phenylethane. The reagent used is sodium amide in liquid ammonia cause dehydrohalogenation.

(k)

Interpretation Introduction

Interpretation:

Synthesis of 1-phenyl-4-penten-1-yne has to be shown.

Concept Introduction:

1-phenyl-4-penten-1-yne can be prepared from phenylethyne and prop-2-en-1-ol.  Carbon-carbon coupling will occur by using these reagents.

(l)

Interpretation Introduction

Interpretation:

Synthesis of 1-phenyloctyne has to be shown.

Concept Introduction:

1-phenyloctyne can be synthesized from phenylethyne through two steps.  In the first step phenylethyne treated with Grignard reagent to get 1-phenylethyne magnesium bromide which then react with hexyl iodide in second step to give 1-phenyloctyne.

(m)

Interpretation Introduction

Interpretation:

$\text{(E)-1-phenyloct-1-ene}$ has to be synthesized.

Concept Introduction:

$\text{(E)-1-phenyloct-1-ene}$ can be synthesized from 1-phenyloctyne.  The reagent sodium in liquid ammonia selectively gives trans hydrogenated product.

(n)

Interpretation Introduction

Interpretation:

$\text{(Z)-1-phenyloct-1-ene}$ has to be synthesized.

Concept Introduction:

$\text{(Z)-1-phenyloct-1-ene}$ can be synthesized from 1-phenyl octyne.  The reagent Lindlar’s catalyst selectively gives cis hydrogenated product.  Lindlar’s catalyst is a mixture of $Pd,CaC{O}_3,Pb\text{}saltandquinolines.$