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Chapter 27: Problem 24

Predict the products of the following reactions. Assume that \([\mathrm{O}]\) represents \(\mathrm{Na}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}\) in \(\mathrm{H}_{2} \mathrm{SO}_{4}:\) (a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}_{2} \mathrm{OH} \stackrel{[\mathrm{O}]}{\longrightarrow}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}+\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCOOH} \frac{\mathrm{H}^{+}}{\Delta}\) (c) 3 -methyl- 2 -butanol \(+\mathrm{NaCl} \stackrel{\mathrm{H}_{2} \mathrm{SO}_{4}}{\longrightarrow}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH} \frac{\mathrm{H}_{2} \mathrm{SO}_{4}}{\Delta}\)

Short Answer

Expert verified
The predicted products are: (a) \( (CH_3)_2CHCHO \), (b) \( CH_3CH_2OOC(CH_3)_2CH_2 \), (c) 3-chloro-2-methylbutane, and (d) \( CH_3CHOCH_2CH_3 \).

Step by step solution

01

Identify the Type of Each Reaction and the Functional Groups

In (a), the reagent Na2Cr2O7 in H2SO4 is involved; this is an oxidizing agent. The molecule has a primary alcohol group. In (b), the presence of \( H^+ \) suggests an acid-catalyzed reaction and the two of the molecules contain a primary alcohol group and a carboxylic acid group. In (c), the presence of \( H_2SO_4 \) and sodium chloride (NaCl) suggests this may be a substitution reaction involving 3 -methyl- 2 -butanol. Lastly, in (d), \( H_2SO_4 \) indicates a dehydration reaction, and the molecule is a primary alcohol.
02

Predict the Products

For (a), oxidation of a primary alcohol results in an aldehyde. Therefore, the product will be \( (CH_3)_2CHCHO \). For (b), the acid-catalyzed reaction will result in esterification, yielding \( CH_3CH_2OOC(CH_3)_2CH_2 \) (an ester). For (c), the substitution reaction in acidic conditions with an alcohol would yield an alkyl halide, therefore the product is 3-chloro-2-methylbutane. For (d), the dehydration of an alcohol in acidic condition would usually produce an alkene, but in this case since it's a primary alcohol, an ether is produced, with the product being \( CH_3CHOCH_2CH_3 \).
03

Verify the Results

Make sure the reactions correspond to the rules for the reaction type. Oxidation of a primary alcohol yields an aldehyde, esterification between a carboxylic acid and an alcohol produces an ester, substitution of an alcohol in acidic conditions yields an alkyl halide, and dehydration of a primary alcohol yields an ether.

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Most popular questions from this chapter

Predict the main product(s) of (a) the mononitration of chlorobenzene; (b) the monosulfonation of nitrobenzene; (c) the monochlorination of 1-methyl-2-nitrobenzene

Indicate the principal product(s) you would expect in (a) treating \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}\) with dilute \(\mathrm{H}_{2} \mathrm{SO}_{4}(\mathrm{aq})\) (b) exposing a mixture of chlorine and propane gases to ultraviolet light; (c) heating a mixture of isopropyl alcohol and benzoic acid; (d) oxidizing sec-butyl alcohol with \(\mathrm{Cr}_{2} \mathrm{O}_{7}^{2-}\) in acidic solution.

Draw a structure to represent the principal product of each of the following reactions: (a) 1 -pentanol \(+\) dichromate ion (acid solution) (b) butyric acid + ethanol (acid solution) (c) 2 -methyl-1-butene \(+\mathrm{HBr}\)

Predict the products of the monobromination of (a) \(m\) -dinitrobenzene; (b) aniline; (c) \(p\) -bromoanisole.

Predict the main product(s) of (a) the mononitration of benzoic acid; (b) the monosulfonation of phenol; (c) the monobromination of 2 -nitrobenzaldehyde.
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