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Chapter 27: Problem 75

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. $$\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}=\mathrm{CH}_{2} \stackrel{\mathrm{H}_{2} \mathrm{SO}_{4}, \mathrm{H}_{2} \mathrm{O}}{\longrightarrow}$$

Short Answer

Expert verified
The reaction of 2-methyl-1-butene with sulfuric acid and water yields 2-methyl-2-butanol. This involves a protonation step to form a carbocation, a nucleophilic attack by water, and a deprotonation step to form the alcohol.

Step by step solution

01

Protonation

Protonate the alkene in 2-methyl-1-butene using a proton (H+) from sulfuric acid (H2SO4) makes a positive carbocation. As a general rule, the proton will attach to the carbon atom that results in the most stable carbocation. In this case, that will be the secondary carbon atom, not part of the methyl group. After protonation, you get (CH3)2C+(CH2)CH3.
02

Nucleophilic attack

The carbocation will undergo a nucleophilic attack by a water molecule. Water, being a stronger nucleophile, donates an electron pair to form a bond with the positively charged carbon atom. The resulting species is (CH3)2C(OH)(CH2)CH3 positively charged since it retains one proton from water.
03

Deprotonation

A second water molecule will now act as a base, it removes the extra proton (H+) from the carbon bearing the hydroxyl group (OH). The result is a neutral alcohol - 2-methyl-2-butanol.

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Most popular questions from this chapter

A sample of \((R)-\mathrm{CH}_{3} \mathrm{CH}(\mathrm{Cl}) \mathrm{CH}_{2} \mathrm{CH}_{3}\) reacts with \(\mathrm{CH}_{3} \mathrm{S}^{-}\) in dimethyl sulfoxide, and the resulting solution is optically active. (a) Write the formula of the product. (b) By which mechanism does this nucleophilic substitution reaction occur?

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 \(\mathrm{CCl}_{4}\)

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.

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

Which of the following reactions would give a better yield of \(\mathrm{CH}_{3} \mathrm{OCH}\left(\mathrm{CH}_{3}\right)_{2} ?\) Explain. \(\mathrm{CH}_{3} \mathrm{ONa}+\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHI} \longrightarrow \mathrm{CH}_{3} \mathrm{OCH}\left(\mathrm{CH}_{3}\right)_{2}+\mathrm{NaI}\) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHONa}+\mathrm{CH}_{3} \mathrm{I} \longrightarrow \mathrm{CH}_{3} \mathrm{OCH}\left(\mathrm{CH}_{3}\right)_{2}+\mathrm{NaI}\)
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