Consider the following reactions. For parts \(\mathrm{b}-\mathrm{d}\), see Exercise 62 . a. When \(\mathrm{C}_{5} \mathrm{H}_{12}\) is reacted with \(\mathrm{Cl}_{2}(g)\) in the presence of ultraviolet light, four different monochlorination products form. What is the structure of \(\mathrm{C}_{5} \mathrm{H}_{12}\) in this reaction? b. When \(\mathrm{C}_{4} \mathrm{H}_{8}\) is reacted with \(\mathrm{H}_{2} \mathrm{O}\), a tertiary alcohol is produced as the major product. What is the structure of \(\mathrm{C}_{4} \mathrm{H}_{8}\) in this reaction? c. When \(\mathrm{C}_{7} \mathrm{H}_{12}\) is reacted with HCl, 1 -chloro-1-methylcyclohexane is produced as the major product. What are the two possible structures for \(\mathrm{C}_{7} \mathrm{H}_{12}\) in this reaction? d. When a hydrocarbon is reacted with \(\mathrm{H}_{2} \mathrm{O}\) and the major product of this reaction is then oxidized, acetone (2-propanone) is produced. What is the structure of the hydrocarbon in this reaction? e. When \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\) is oxidized, a carboxylic acid is produced. What are the possible structures for \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\) in this reaction?

Step by step solution

01

Analyze molecular formula

We are given the molecular formula for the hydrocarbon reactant, C5H12. This is an alkane with 5 carbon atoms, as the general formula for alkanes is CnH2n+2.

02

Identify the alkane

The alkane with 5 carbon atoms is called pentane. The structure of pentane is a straight chain of 5 carbon atoms connected with single bonds: CH3-CH2-CH2-CH2-CH3. b. Structure of C4H8 in reaction with H2O

03

Analyze molecular formula

We are given the molecular formula for the hydrocarbon reactant, C4H8. This is an alkene with 4 carbon atoms, as the general formula for alkenes is CnH2n.

04

Identify the alkene leading to tertiary alcohol

In the presence of an acid catalyst, the alkene can undergo hydroxylation to form an alcohol. Since a tertiary alcohol is produced, the reaction must involve a double bond in the alkene next to a tertiary carbon. The only 4-carbon alkene with this condition is 2-methylpropene. c. Possible structures for C7H12

05

Analyze molecular formula

We are given the molecular formula for the hydrocarbon reactant, C7H12. We also know that the major product of its reaction with HCl is 1-chloro-1-methylcyclohexane.

06

Identify the possible structures of hydrocarbon

There are two possible structures that could result in the given product when they react with HCl: 1-methyl-1-cyclohexene and 3-methyl-1-cyclohexene. In both cases, the reaction with HCl will create a carbocation adjacent to the double bond. Chloride ion will then attack the carbocation to form the product. d. Structure of the hydrocarbon in the reaction

07

Analyze reaction with H2O and the oxidation product

The hydrocarbon reacts with H2O to produce a major product that is then oxidized to form acetone (2-propanone).

08

Identify the hydrocarbon structure

If the oxidation of the major product results in acetone, the initial hydrocarbon must be an alkene. The only possible structure that meets the conditions in this problem is 2-methylpropene. When it undergoes hydroxylation with H2O, it forms 2-methyl-2-propanol, which can be oxidized to give 2-propanone. e. Possible structures for C5H12O

09

Analyze molecular formula

We are given the molecular formula for the hydrocarbon reactant, C5H12O. We are asked to determine the possible structures for this compound such that a carboxylic acid is formed upon oxidation.

10

Identify the possible alcohol structures

The oxidation of a primary alcohol yields a carboxylic acid. Therefore, we need to identify the possible primary alcohol structures with the given molecular formula. There are three possibilities: 1-pentanol, 2-methyl-1-butanol, and 3-methyl-1-butanol.

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