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Chapter 27: Problem 33

Give the major product that forms when (Z)-3-methyl2-pentene reacts with each of the following reagents: (a) \(\mathrm{HI} ;\) (b) \(\mathrm{H}_{2}\) in the presence of a platinum catalyst; (c) \(\mathrm{H}_{2} \mathrm{O}\) in \(\mathrm{H}_{2} \mathrm{SO}_{4} ;\) (d) \(\mathrm{Br}_{2}\) in \(\mathrm{CCl}_{4}\).

Short Answer

Expert verified
The major products of the reactions are as follows: (a) 2-iodo-3-methylpentane, (b) 3-methylpentane, (c) 2-methyl-3-pentanol, and (d) (2R, 3R)-2,3-dibromo-3-methylpentane and its enantiomer (2S, 3S)-2,3-dibromo-3-methylpentane.

Step by step solution

01

Reaction with Hydroiodic Acid (\(\mathrm{HI}\))

The reaction with \(HI\) will follow Markovnikov's rule, with the halogen attaching to the most substituted carbon of the alkene. The iodine will attach to the tertiary carbon, resulting in 2-iodo-3-methylpentane as the major product.
02

Reaction with Hydrogen (\(\mathrm{H}_{2}\)) in the Presence of a Platinum Catalyst

The reaction with hydrogen gas in the presence of a platinum catalyst will result in the hydrogenation of the alkene, leading to the addition of hydrogen across the double bond. This will yield 3-methylpentane.
03

Reaction with Water (\(\mathrm{H}_{2}\mathrm{O}\)) in \(\mathrm{H}_{2}\mathrm{SO}_{4}\)

The reaction with water in the presence of sulphuric acid will lead to the hydration of the alkene, following Markovnikov's rule. This will result in the formation of 2-methyl-3-pentanol.
04

Reaction with Bromine (\(\mathrm{Br}_{2}\)) in \(\mathrm{CCl}_{4}\)

The reaction with bromine in carbon tetrachloride will lead to the addition of bromine across the double bond in an anti fashion, resulting in the formation of (2R, 3R)-2,3-dibromo-3-methylpentane and its enantiomer (2S, 3S)-2,3-dibromo-3-methylpentane.

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Most popular questions from this chapter

The cyanide anion is a nucleophile and when attached to a carbon atom, undergoes hydrolysis under basic conditions to the carboxylate anion. Suggest a method of preparing sodium butanoate from chloropropane. How can sodium butanoate be converted into butanoic acid?

Predict and name the product(s) obtained from the following reaction. Write out the mechanism for the reaction and use curved arrows to show the movement of electrons. $$\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}=\mathrm{CH}_{2} \stackrel{\mathrm{H}_{2} \mathrm{SO}_{4}, \mathrm{H}_{2} \mathrm{O}}{\longrightarrow}$$

Write the structures of the isomers you would expect to obtain in the mononitration of \(m\) -methoxybenzaldehyde:

Answer the following questions for this E1 reaction: $$\begin{array}{c} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{Br}+\mathrm{CH}_{3} \mathrm{OH} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}=\mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}+\mathrm{Br}^{-}+\mathrm{CH}_{3} \mathrm{OH}_{2}^{+} \end{array}$$ (a) What is the rate expression for the reaction? (b) Draw the reaction profile for the reaction. Label all parts. Assume that the products are lower in energy than the reactants. (c) What is the effect on the rate of the reaction of doubling the concentration of \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{Br} ?\) (d) What is the effect on the rate of the reaction of doubling the concentration of \(\mathrm{CH}_{3} \mathrm{OH} ?\)

Identify the nucleophile, electrophile, and leaving group in each of the following substitution reactions. Predict whether equilibrium favors the reactants or products: (a) \(\mathrm{CH}_{3} \mathrm{OH}+\mathrm{I}^{-} \rightleftharpoons \mathrm{CH}_{3} \mathrm{OH}+\mathrm{NaOH}\) (b) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCl}+\mathrm{KCN} \rightleftharpoons\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCN}+\mathrm{KCl}\)
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