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Chapter 12: Problem 258

Suggest possible routes for the synthesis of the following compounds:

Short Answer

Expert verified
Example 1: Synthesis of 1-Methylcyclohexene can be achieved by dehydrating 1-Methylcyclohexanol using concentrated sulfuric acid (H2SO4) as a catalyst: \(1-Methylcyclohexanol + H_2SO_4 (conc.) \rightarrow 1-Methylcyclohexene + H_2O\). Example 2: Synthesis of Acetophenone can be achieved by Friedel-Crafts acylation of benzene using acetyl chloride and aluminum chloride (AlCl3) as a catalyst: \(Benzene + Acetyl\ Chloride + AlCl_3 \rightarrow Acetophenone + HCl + AlCl_3\).

Step by step solution

01

Identify the Functional Groups

1-Methylcyclohexene is an alkene with a methyl group attached to the cyclohexene ring. The key functional group in this molecule is the carbon-carbon double bond (C=C).
02

Identify Potential Precursors

One possible route to synthesize 1-methylcyclohexene is by dehydration of an alcohol. In this case, we'll need the alcohol precursor: 1-Methylcyclohexanol.
03

Choose the Appropriate Reaction

In order to convert the alcohol (1-methylcyclohexanol) to the desired alkene (1-methylcyclohexene), we'll use an elimination reaction, specifically dehydration. A suitable reagent for this reaction is concentrated sulfuric acid (H2SO4), which will act as a catalyst for the elimination reaction.
04

Write the Reaction Sequence

The overall synthesis can be summarized as follows: 1-Methylcyclohexanol + H2SO4 (conc.) -> 1-Methylcyclohexene + H2O Example 2: Synthesis of Acetophenone
05

Identify the Functional Groups

Acetophenone is an aromatic ketone derived from benzene. The key functional group in this molecule is the carbonyl group (C=O).
06

Identify Potential Precursors

A possible route to synthesize acetophenone is by Friedel-Crafts acylation of benzene. In this case, we'll need the benzene ring as a substrate and an acid chloride (acetyl chloride) as the acylating agent.
07

Choose the Appropriate Reaction

In order to convert benzene to the desired ketone (acetophenone), we'll use Friedel-Crafts acylation. A suitable catalyst for this reaction is aluminum chloride (AlCl3), which will promote the electrophilic attack on the benzene ring.
08

Write the Reaction Sequence

The overall synthesis can be summarized as follows: Benzene + Acetyl Chloride + AlCl3 -> Acetophenone + HCl + AlCl3

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Most popular questions from this chapter

The compound indene, \(\mathrm{C}_{9} \mathrm{H}_{8}\), found in coal tar, rapidly decolorizes \(\mathrm{Br}_{2} / \mathrm{CCl}_{4}\) and dilute \(\mathrm{KMnO}_{4}\). Only one mole of hydrogen is absorbed readily to form indane, \(\mathrm{C}_{9} \mathrm{H}_{10}\). More vigorous hydrogenation yields a compound of formula \(\mathrm{C}_{9} \mathrm{H}_{16} .\) Vigorous oxidation of indene yields phthalic acid. What is the structure of indene? Of indane?

Show how to make the following conversions using any necessary reagents: (a) Benzene to ethylbenzene (b) Toluene to benzyl alcohol (c) Iodobenzene to benzene

Treatment with methyl chloride and \(\mathrm{AICI}_{3}\) at \(0^{\circ}\) converts toluene chiefly into o- and p-xylenes; at \(80^{\circ}\), however, the chief product is \(\mathrm{m}\) -xylene. Furthermore, either o- or \(\mathrm{p}\) -xylene is readily converted into \(\mathrm{m}\) -xylene.by treatment with \(\mathrm{AICI}_{3}\) and \(\mathrm{HCl}\) at \(80^{\circ}\). How do you account for this effect of temperature on orientation? Suggest a role for the HCl.

What would you predict for the general character of the chemical shifts of the protons of (a) the separate \(\mathrm{CH}_{2}\) groups of 1,4 -hexamethylenebenzene as compared with 1,2 -hexamethylenebenzene; 1,4 -hexamethylenebenzene 1,2 -hexamethylenebenzene (b) cyclodctatetraene

tert-Pentylbenzene is the major product of the reaction of benzene in the presence of \(\mathrm{BF}_{3}\) with each of the following alcohols; (a) 2 -methyl-1-butanol, (b) 3 -methyl-2-butanol, (c) 3 -methyl-1-butanol, and (d) neopentyl alcohol. Account for its formation in each case.
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