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Which of the following would be the worst solvent for an SN2 reaction (slowest rate)? N. 0=

Which of the following would be the worst solvent for an SN2 reaction (slowest rate)? N. 0=

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
Problem 15CTQ
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**Question:** Which of the following would be the worst solvent for an S<sub>N</sub>2 reaction (slowest rate)? **Options:** 1. **Acetone** - **Structure:** A three-carbon chain with a carbonyl group (C=O) at the central carbon. 2. **Ethanol** - **Structure:** A two-carbon chain with a hydroxyl group (OH) attached to the terminal carbon. 3. **Dimethyl Sulfoxide (DMSO)** - **Structure:** A sulfur atom double bonded to an oxygen (S=O) and single bonded to two methyl groups. 4. **N,N-Dimethylformamide (DMF)** - **Structure:** A formamide group (O=C—N) with both hydrogen atoms on nitrogen replaced by methyl groups. In an S<sub>N</sub>2 reaction, polar aprotic solvents like acetone, DMSO, and DMF generally increase reaction rates because they don’t solvate nucleophiles as strongly as polar protic solvents like ethanol. The worst solvent for S<sub>N</sub>2 reactions would typically be the polar protic solvent, which is ethanol in this list, due to its tendency to form hydrogen bonds and solvate nucleophiles, slowing down the reaction.
Transcribed Image Text:**Question:** Which of the following would be the worst solvent for an S<sub>N</sub>2 reaction (slowest rate)? **Options:** 1. **Acetone** - **Structure:** A three-carbon chain with a carbonyl group (C=O) at the central carbon. 2. **Ethanol** - **Structure:** A two-carbon chain with a hydroxyl group (OH) attached to the terminal carbon. 3. **Dimethyl Sulfoxide (DMSO)** - **Structure:** A sulfur atom double bonded to an oxygen (S=O) and single bonded to two methyl groups. 4. **N,N-Dimethylformamide (DMF)** - **Structure:** A formamide group (O=C—N) with both hydrogen atoms on nitrogen replaced by methyl groups. In an S<sub>N</sub>2 reaction, polar aprotic solvents like acetone, DMSO, and DMF generally increase reaction rates because they don’t solvate nucleophiles as strongly as polar protic solvents like ethanol. The worst solvent for S<sub>N</sub>2 reactions would typically be the polar protic solvent, which is ethanol in this list, due to its tendency to form hydrogen bonds and solvate nucleophiles, slowing down the reaction.
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