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Chapter 27: Problem 55

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 \(+\mathrm{HBr}\)

Short Answer

Expert verified
The principal products of the reactions are: (a) Pentanal, (b) Ethyl butanoate, (c) 2-bromo-2-methylbutane.

Step by step solution

01

Oxidation of 1-Pentanol

Addition of dichromate ion to 1-pentanol under acidic conditions results in the oxidation of the alcohol to a carbonyl compound. Depending on the conditions, this can either lead to an aldehyde or a carboxylic acid. In this case, the aldehyde or carbonyl compound formed is pentanal.
02

Esterification of Butyric acid and Ethanol

Butyric acid and ethanol react under acidic conditions to form an ester via an esterification reaction. The acid part comes from the butyric acid which contributes a 4 carbon chain, and the alcohol part comes from the ethanol which contributes a 2 carbon chain. The ester linkage is a carbonyl group adjacent to an ether linkage. The resultant ester is ethyl butanoate.
03

Addition of HBr to 2-Methyl-1-Butene

Hydrobromic acid (HBr) adds to the carbon-carbon double bond of 2-methyl-1-butene. In this reaction, the more stable carbocation intermediate is the one where the positive charge is on the more substituted carbon. Thus, the bromine prefers to attach at the tertiary carbon end (3rd carbon). The result is 2-bromo-2-methylbutane.

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Most popular questions from this chapter

Write the name and structure of the benzene derivatives described below. (a) Formula: \(\mathrm{C}_{8} \mathrm{H}_{10} ;\) forms three monochlorination products when treated with \(\mathrm{Cl}_{2}\) and \(\mathrm{FeCl}_{3}\) (b) Formula: \(\mathrm{C}_{9} \mathrm{H}_{12}\); forms one monochlorination product when treated with \(\mathrm{Cl}_{2}\) and \(\mathrm{FeCl}_{3}\) (c) Formula: \(\mathrm{C}_{9} \mathrm{H}_{12}\); forms four monochlorination products when treated with \(\mathrm{Cl}_{2}\) and \(\mathrm{FeCl}_{3}\)

Write a balanced chemical equation for the reaction that is described and then classify the reaction as a substitution, an elimination, an addition, or a rearrangement reaction: (a) Ethene and \(\mathrm{Br}_{2}\) react in carbon tetrachloride to give 1,2 -dibromoethane. (b) Iodoethane reacts with KOH(aq) yielding ethene, water, and potassium bromide. (c) Chloromethane reacts with \(\mathrm{NaOH}(\) aq) to give methanol and sodium chloride.

What is major product expected from the monobromination of 2,2,3 -trimethylpentane?

The three isomeric tribromobenzenes, I, II, and III, when nitrated, form three, two, and one mononitrotribromobenzenes, respectively. Assign correct structures to I, II, and III.

Write equations for the substitution reaction of \(n\) -bromobutane, a typical primary haloalkane, with the following reagents: (a) \(\mathrm{NaOH} ;\) (b) \(\mathrm{NH}_{3} ;\) (c) \(\mathrm{NaCN}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{ONa}\).
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