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Chapter 27: Problem 58

Write the formulas of the products formed from the reaction of 2 -butene with each of the following substances: (a) \(\mathrm{H}_{2} ;\) (b) \(\mathrm{Cl}_{2} ;\) (c) \(\mathrm{HCl} ;\) (d) \(\mathrm{H}_{2} \mathrm{O}\) (in acid).

Short Answer

Expert verified
The products formed from the reaction of 2-butene with the given substances are: (a) butane, (b) 2,3-dichlorobutane, (c) 2-chlorobutane, and (d) 2-butanol.

Step by step solution

01

Hydrogenation of 2-Butene

Reaction (a) is an example of hydrogenation, where molecular hydrogen (\(\mathrm{H}_2\)) is added to the alkene. In this case, hydrogen is added to 2-butene, resulting in butane. This reaction removes the double bond and turns the alkene into an alkane. The general formula for this reaction is \( \mathrm{RCH=CHR} + \mathrm{H}_2 \rightarrow \mathrm{RCH}_2\mathrm{CHR}_2\). Replace \(\mathrm{R}\) with an ethyl group (\(\mathrm{-CH_2CH_3}\)) to get the product for this specific case, which will yield butane (\(\mathrm{C}_4\mathrm{H}_{10}\)).
02

Halogenation of 2-Butene

Reaction (b) is a halogenation reaction, where a halogen is added across the double bond in the alkene. In 2-butene's case, it reacts with \(\mathrm{Cl}_2\) to form 2,3-dichlorobutane. The general formula is \(\mathrm{RCH=CHR} + \mathrm{X}_2 \rightarrow \mathrm{RCHX-CHXR}\). Replace \(\mathrm{R}\) with an ethyl group (\(\mathrm{-CH_2CH_3}\)) and \(\mathrm{X}\) with a Chlorine atom (\(\mathrm{Cl}\)), and this will yield 2,3-dichlorobutane (\(\mathrm{C}_4\mathrm{H}_8\mathrm{Cl}_2\)).
03

Hydrohalogenation of 2-Butene

Reaction (c) is a hydrohalogenation reaction, where a hydrogen halide (in this case \(\mathrm{HCl}\)) is added to the alkene. This results in 2-chlorobutane. For this specific case, follow the general equation \(\mathrm{RCH=CHR} + \mathrm{HX} \rightarrow \mathrm{RCHX-CH_2R}\). Again, replace \(\mathrm{R}\) with an ethyl group (\(\mathrm{-CH_2CH_3}\)) and \(\mathrm{X}\) with a Chlorine atom (\(\mathrm{Cl}\)), and the product is 2-chlorobutane (\(\mathrm{C}_4\mathrm{H}_9\mathrm{Cl}\)).
04

Hydration of 2-Butene

Finally, for reaction (d), 2-butene undergoes hydration in the presence of an acid to form 2-butanol. This is the general reaction \(\mathrm{RCH=CHR} + \mathrm{H}_2\mathrm{O} \rightarrow \mathrm{RCHOH-CH_2R}\). Replacing \(\mathrm{R}\) with an ethyl group (\(\mathrm{-CH_2CH_3}\)) will yield 2-butanol (\(\mathrm{C}_4\mathrm{H}_9\mathrm{OH}\)).

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Most popular questions from this chapter

Which of the following is the strongest nucleophile for an \(S_{N} 2\) reaction? (a) \(\mathrm{H}_{2} \mathrm{O} ;\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH};\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{O}^{-} ;\) (d) \(\mathrm{CH}_{3} \mathrm{CO}_{2}{^-} ;\) (e) \(\mathrm{CH}_{3} \mathrm{S}^{-}\)

Answer the following questions for this \(\mathrm{S}_{\mathrm{N}}1\) reaction: (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 1-bromo-1-methylpentane? (d) The solvent for the reaction is ethanol. What is the effect on the rate of the reaction of adding more ethanol?

Explain the important distinctions between each pair of terms: (a) base and nucleophile; (b) \(\alpha\) carbon and \(\beta\) carbon; (c) polar protic solvent and polar aprotic solvent; (d) carbocation and radical.

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) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{ONa}\).

Write the initiation, propagation, and termination steps involved in the monobromination of \(2,3-\) dimethylbutane to give 2 -bromo- 2,3 -dimethylbutane.
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