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For S N 1 reaction, when do you put a dash or wedge?

A) Dash indicates the major product, wedge indicates the minor product
B) Wedge indicates the major product, dash indicates the minor product
C) It depends on the nucleophile
D) Neither dash nor wedge is used

User Zaus
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Dashes and wedges in an SN1 reaction are used to depict the three-dimensional spatial arrangement of substituents, not to indicate major or minor products. Since the carbocation intermediate can be attacked from either side, both enantiomers are formed, resulting in a racemic mixture without a major or minor product.

When discussing an SN1 reaction, the choice to use a dash or a wedge does not indicate major or minor products. Instead, dashes and wedges are used to represent the three-dimensional orientation of substituents coming off a chiral center in a molecule. In the case of an SN1 reaction, a carbocation intermediate is formed which is planar and can be attacked from either side by the nucleophile. This results in the formation of products that are enantiomers, with wedges indicating substituents coming out of the plane towards you and dashes indicating substituents going behind the plane away from you. Because the carbocation intermediate can be attacked from either side with equal probability, it leads to a racemic mixture of products, meaning neither dash nor wedge indicates the major product, as both are formed in equal amounts in such reactions.

Stereoselectivity of Electrophilic Addition Reactions

Stereoselectivity occurs when a reaction forms a chiral, or "handed", product from achiral reactants and catalysts. For example, during electrophilic addition reactions to alkenes that generate a chiral product, the reaction is not selective and therefore produces both enantiomers in equal amount because the nucleophile can attack a trigonal planar carbocation intermediate from either side of the plane, resulting in a racemic mixture of the (R) and (S) configurations.

User Matthew Smart
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