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Chapter 27: Problem 34

Give the major product that forms when 1 -ethylcyclohexene 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 are: (a) 1-ethyl-1-iodocyclohexane, (b) ethylcyclohexane, (c) 1-ethylcyclohexanol, and (d) 1,2-dibromo-1-ethylcyclohexane.

Step by step solution

01

Reaction with Hydroiodic Acid

When HI is added to an alkene, it undergoes electrophilic addition. The hydrogen atom of HI adds to one of the carbons of the double bond and the Iodine atom to the other carbon. Resulting in the formation of 1-ethyl-1-iodocyclohexane.
02

Reaction with Hydrogen Gas in the Presence of a Platinum Catalyst

Hydrogenation of alkenes with a platinum catalyst leads to the addition of hydrogen molecules across the double bond. This is a reduction reaction where two hydrogen atoms add to the two carbon atoms of the double bond in a syn addition manner. Resulting in the formation of ethylcyclohexane.
03

Reaction with Water in Sulfuric Acid

Water in the presence of sulfuric acid (a strong acid) results in the formation of hydronium ions (H3O+). This acid catalyzed hydration of alkene results in the addition of a hydroxyl group (-OH) and a hydrogen atom across the double bond, with the alcohol functional group forming at the more substituted carbon atoms following Markovnikov's rule. This results in the formation of 1-ethylcyclohexanol.
04

Reaction with Bromine in Carbon Tetrachloride

Bromine (Br2) in an inert solvent like carbon tetrachloride (CCl4) causes halogenation of alkenes. It is an electrophilic addition reaction where a bromine molecule adds across the double bond to form a vicinal dibromide. This yields 1,2-dibromo-1-ethylcyclohexane.

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Most popular questions from this chapter

Predict the product(s) of the reaction of: (a) HCl with 2-chloro-1-propene (b) HCN with \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}_{2}\) (c) HCl with CH \(_{3} \mathrm{CH}=\mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}\)

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) 3,3 -dimethyl- 1 -butene reacts in acid solution to yield 2,3-dimethyl-2-butene. (b) 1 -iodo-2,2-dimethylpropane reacts with water, 2,2-dimethyl-1-propanol, and HI(aq). (c) 2-chloro-2-methylpropane reacts with NaOH(aq) to give 2 -methyl- 1 -propene, sodium chloride, and water.

To prepare methyl ethyl ketone, which of these compounds would you oxidize: 2 -propanol, 1 -butanol, 2-butanol, or tert-butyl alcohol? Explain.

Answer the following questions for this E2 reaction: $$\begin{aligned} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}+\mathrm{NaOH} & \longrightarrow \mathrm{CH}_{3} \mathrm{CH}= \mathrm{CH}_{2}+\mathrm{NaBr}+\mathrm{H}_{2} \mathrm{O} \end{aligned}$$ (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 \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br} ?\) (d) What is the effect on the rate of the reaction of halving the concentration of \(\mathrm{NaOH} ?\)

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?
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