What is the purpose of CH3OH being the solvent? Isn't CH3S- the only reagent needed in order to go through an SN2 reaction with the replacement of the bromine?

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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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What is the purpose of CH3OH being the solvent? Isn't CH3S- the only reagent needed in order to go through an SN2 reaction with the replacement of the bromine?

**Text Transcription for Educational Use:**

Sulfur, being larger and more polarizable than oxygen, makes thiolate ions superior nucleophiles compared to alkoxide ions. Due to their effectiveness, thiolates are capable of reacting with secondary alkyl halides to produce favorable yields of S<sub>N</sub>2 products.

**Chemical Reaction Explanation:**

The reaction illustrated involves (R)-2-bromobutane, characterized by a bromine (Br) atom bonded to a carbon center, which carries a hydrogen (H), a methyl (CH<sub>3</sub>), and an ethyl (CH<sub>2</sub>CH<sub>3</sub>) group.

The reagent, sodium methyl thiolate (CH<sub>3</sub>S<sup>&minus;</sup>Na<sup>&#43;</sup>) in methanol (CH<sub>3</sub>OH), facilitates the nucleophilic substitution. The bromine is displaced by a methanethiol group (SCH<sub>3</sub>), yielding (S)-2-(methylthio)butane.

The stereochemistry is important to note in the structures where wedge and dash notations show the spatial arrangement, illustrating a change in configuration from R (rectus) to S (sinister) due to the S<sub>N</sub>2 mechanism.
Transcribed Image Text:**Text Transcription for Educational Use:** Sulfur, being larger and more polarizable than oxygen, makes thiolate ions superior nucleophiles compared to alkoxide ions. Due to their effectiveness, thiolates are capable of reacting with secondary alkyl halides to produce favorable yields of S<sub>N</sub>2 products. **Chemical Reaction Explanation:** The reaction illustrated involves (R)-2-bromobutane, characterized by a bromine (Br) atom bonded to a carbon center, which carries a hydrogen (H), a methyl (CH<sub>3</sub>), and an ethyl (CH<sub>2</sub>CH<sub>3</sub>) group. The reagent, sodium methyl thiolate (CH<sub>3</sub>S<sup>&minus;</sup>Na<sup>&#43;</sup>) in methanol (CH<sub>3</sub>OH), facilitates the nucleophilic substitution. The bromine is displaced by a methanethiol group (SCH<sub>3</sub>), yielding (S)-2-(methylthio)butane. The stereochemistry is important to note in the structures where wedge and dash notations show the spatial arrangement, illustrating a change in configuration from R (rectus) to S (sinister) due to the S<sub>N</sub>2 mechanism.
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