Consider the substitution reaction that takes place when (R)-3-bromo-3-methylhexane is treated with methanol. Which of the following would be true? A) The reaction would take place only with inversion of configuration at the stereogenic center. B) The reaction would take place only with retention of configuration at the stereogenic center. C) The reaction would take place with racemization. D) No reaction would take place. E) The alkyl halide does not possess a stereogenic center. a. А b. B c. C d. D e. Е

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14-11-2022
Chemistry

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Consider the substitution reaction that takes place when (R)-3-bromo-3-methylhexane is treated with methanol. Which of the following would be true? A) The reaction would take place only with inversion of configuration at the stereogenic center. B) The reaction would take place only with retention of configuration at the stereogenic center. C) The reaction would take place with racemization. D) No reaction would take place. E) The alkyl halide does not possess a stereogenic center. a. А b. B c. C d. D e. Е

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kjuli1766 kjuli1766 · Answer 1 · 2022-11-18T12:19:45+01:00

The reaction would take place with racemization. Option C.

The reaction between (s)-3-Bromo-3-methyl hexane and water is a nucleophilic substitution reaction as the leaving group present on the substrate is displaced by a nucleophile. Water is a polar protic solvent and he prefers SN1 reactions over SN2 reactions. Therefore, the reaction mechanism is SN1.

The carbocation and its substituents are all in the same plane. In other words, the nucleophile can attack from either side. As a result, both enantiomers are formed in the SN1 reaction, producing a racemic mixture of both enantiomers. Alkenes react with pure liquid bromine at low temperatures or with solutions of bromine in organic solvents such as carbon tetrachloride. The double bond is broken and a bromine atom is attached to each carbon atom.

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