problem 8.13 Draw the complete mechanism and the products for each of the following S2 reactions, paying close attention to stereochemistry. ONCHas Br ? ? CH3 (a) (b) Br Br (CHs),P: ? (c)

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do 8.13!

**Problem 8.13**

Draw the complete mechanism and the products for each of the following S<sub>N</sub>2 reactions, paying close attention to stereochemistry.

**(a)** A bromine-substituted alkane reacting with iodide ion (I<sup>-</sup>).

- Reactants: A secondary alkyl bromide with a wedge symbol indicating stereochemistry, reacting with iodide ion.
- Expected to result in a product where the iodide ion replaces the bromine atom, with inversion of stereochemistry.

**(b)** A cyclic ammonium salt reacting with bromide ion (Br<sup>-</sup>).

- Reactants: A cyclic structure with a trimethylammonium group and methyl on one carbon, reacting with bromide ion.
- Expected to result in the bromide replacing the ammonium group, with specific stereochemical outcome.

**(c)** A benzyl bromide reacting with a phosphine nucleophile ((C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>P:).

- Reactants: A benzyl bromide with stereochemical indication, reacting with triphenylphosphine.
- Expected to yield a substitution product with consideration of the stereochemistry of the reaction.
Transcribed Image Text:**Problem 8.13** Draw the complete mechanism and the products for each of the following S<sub>N</sub>2 reactions, paying close attention to stereochemistry. **(a)** A bromine-substituted alkane reacting with iodide ion (I<sup>-</sup>). - Reactants: A secondary alkyl bromide with a wedge symbol indicating stereochemistry, reacting with iodide ion. - Expected to result in a product where the iodide ion replaces the bromine atom, with inversion of stereochemistry. **(b)** A cyclic ammonium salt reacting with bromide ion (Br<sup>-</sup>). - Reactants: A cyclic structure with a trimethylammonium group and methyl on one carbon, reacting with bromide ion. - Expected to result in the bromide replacing the ammonium group, with specific stereochemical outcome. **(c)** A benzyl bromide reacting with a phosphine nucleophile ((C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>P:). - Reactants: A benzyl bromide with stereochemical indication, reacting with triphenylphosphine. - Expected to yield a substitution product with consideration of the stereochemistry of the reaction.
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