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Chapter 4: Problem 110

Which of the following statement is not correct regarding the solvolysis of 3 -bromo-3-methylhexane? (a) Polar solvents accelerate the reaction. (b) The intermediate involves \(\mathrm{sp}^{2}\) carbon. (c) The rate of the reaction at a particular temperature depends only on the concentration of \(3-\) Bromo- \(3-\) methyl hexane. (d) The reaction involves inversion of configuration.

Short Answer

Expert verified
a) Polar solvents accelerate the reaction. b) The intermediate involves \(\mathrm{sp}^{2}\) carbon. c) The rate of the reaction at a particular temperature depends only on the concentration of 3-bromo-3-methylhexane. d) The reaction involves inversion of configuration. Answer: d) The reaction involves inversion of configuration.

Step by step solution

01

Understanding the solvolysis mechanism

The solvolysis of 3-bromo-3-methylhexane involves a nucleophilic substitution reaction, specifically an SN1 reaction. In this mechanism, the reaction occurs in two steps: (1) the leaving group (bromide ion) departs, forming a carbocation intermediate, and (2) the nucleophile (usually the solvent) attacks the carbocation, leading to the final product.
02

Analyzing option (a)

Option (a) states that polar solvents accelerate the reaction. This statement is correct. Polar solvents stabilize the carbocation intermediate formed in the SN1 reaction mechanism, lowering the overall activation energy and increasing the reaction rate.
03

Analyzing option (b)

Option (b) states that the intermediate involves \(\mathrm{sp}^{2}\) carbon. This statement is also correct. The carbocation intermediate has a central carbon with three bonds and an empty p orbital, giving it an \(\mathrm{sp}^{2}\) hybridization.
04

Analyzing option (c)

Option (c) states that the rate of the reaction at a particular temperature depends only on the concentration of 3-bromo-3-methylhexane. This statement is correct. The rate law for an SN1 reaction is given by the equation: Rate \(= k \times [\text{3-bromo-3-methylhexane}]\) The rate law only depends on the concentration of the substrate (3-bromo-3-methylhexane) and the reaction rate constant (k), which is temperature-dependent.
05

Analyzing option (d)

Option (d) states that the reaction involves inversion of configuration. This statement is not correct. In an SN1 reaction, the nucleophile can attack the carbocation intermediate from either side, leading to a mixture of retention and inversion of configuration. The product will be a racemic mixture if the starting material is optically active. Hence, the statement that is not correct regarding the solvolysis of 3-bromo-3-methylhexane is option (d).

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