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Chapter 27: Problem 6

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.

Short Answer

Expert verified
(a) is a rearrangement reaction given by the equation \( (CH_3)_3C-CH=CH_2 + H^{+} \rightarrow (CH_3)_3C-CH_2-CH_3 \). (b) is a substitution reaction: \( (CH_3)_3CI + H_2O \rightarrow (CH_3)_3COH + HI \). (c) This is an elimination reaction: \( (CH_3)_3CCl + NaOH \rightarrow (CH_3)_2C=CH_2 + NaCl + H_2O \).

Step by step solution

01

- Reaction (a)

Observing 3,3-dimethyl-1-butene reacts in an acid solution to yield 2,3-dimethyl-2-butene, the process implies a rearrangement occurs. Thus, the reaction can be written as \( (CH_3)_3C-CH=CH_2 + H^{+} \rightarrow (CH_3)_3C-CH_2-CH_3 \). This is considered a rearrangement reaction.
02

- Reaction (b)

1-iodo-2,2-dimethylpropane reacting with water gives 2,2-dimethyl-1-propanol and HI(aq). This can be represented as \( (CH_3)_3CI + H_2O \rightarrow (CH_3)_3COH + HI \). This is a substitution reaction, where iodine has been replaced by hydroxyl group owing to its reaction with water.
03

- Reaction (c)

2-chloro-2-methylpropane reacting with NaOH(aq) gives 2-methyl-1-propene, sodium chloride, and water. The equation for the reaction is \( (CH_3)_3CCl + NaOH \rightarrow (CH_3)_2C=CH_2 + NaCl + H_2O \). This reaction is an elimination reaction, where chlorine on the 2-chloro-2-methylpropane is replaced with a hydrogen, effectively eliminating a molecule of water and forming the double bond in the product.

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Most popular questions from this chapter

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

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 the formulas of the products expected to form in the following situations. If no reaction occurs, write N.R. (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}(\mathrm{aq})+\mathrm{HCl}(\mathrm{aq}) \longrightarrow\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{N}(\mathrm{aq})+\mathrm{HBr}(\mathrm{aq}) \longrightarrow\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{3}^{+}(\mathrm{aq})+\mathrm{H}_{3} \mathrm{O}^{+}(\mathrm{aq}) \longrightarrow\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{3}^{+}(\mathrm{aq})+\mathrm{OH}^{-}(\mathrm{aq}) \longrightarrow\)

(a) Which of the nucleophiles \(\mathrm{CN}^{-}\) or \(\mathrm{Cl}^{-}\) reacts faster with \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{I}\) in an \(\mathrm{S}_{\mathrm{N}} 2\) reaction? (b) Which of the substrates, \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{CH}_{2} \mathrm{I}\) or \(\mathrm{CH}_{3} \mathrm{I},\) reacts faster with \(\mathrm{OH}^{-}\) in an \(\mathrm{S}_{\mathrm{N}}\) 2 reaction?

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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