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QuestionArt
(A) Draw the the sn^2 product for the following nucleophile and the substrate.
hydroxide ion + (R)- 3 -iodoheptane
(B) Select the solvent from the options below you would use to give you the fastest rate for Sn^2.
Water
Dimethyl Sufoxide
Ethanol
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Answer
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Step 1(A) The S$_N$2 reaction involves a backside attack on the substrate by the nucleophile, leading to a substitution and inversion of configuration.
Therefore, I would choose DMSO as the solvent to give the fastest rate for the S$_N$2 reaction between the hydroxide ion and (R)-3-iodoheptane.
The hydroxide ion will attack the carbon atom bonded to the iodine atom in (R)- 3 -iodoheptane. The reaction can be represented as follows: \begin{array}{c} \text { Hydroxide ion } \ \text { (nucleophile) } \ \end{array} + \begin{array}{c} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\right) \mathrm{CH}_{2} \mathrm{I} \ \text { (R)- 3 -iodoheptane } \ \text { (substrate) } \end{array} \longrightarrow \begin{array}{c} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\right) \mathrm{CH}_{2} \mathrm{OH} \ \text { (R)- 3 -hydroxyheptane } \ \text { (S}_N^2 \text { product) } \end{array}
Final Answer
(A) The S$_N$2 product for the given nucleophile and substrate is (R)- 3 -hydroxyheptane. (B) The solvent that would give the fastest rate for the S$_N$2 reaction is Dimethyl sulfoxide (DMSO).
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