Question

I. Identify whether the alkyl halide will undergo elimination (E1 or E2), substitution (SN1 or SN2), or a combination. Explain what led you to your conclusion (3 points) II. Draw the reaction mechanism (include all curved arrows) and identify 1) the nucleophile and electrophile in the first step; and 2) each step as one of the four types: Loss of Leaving group, nucleophilic attack, proton transfer, or rearrangement. If the mechanism is concerted, identify all reaction types occurring during the concerted step. (4 points) III. Discuss the regioselectivity and stereochemistry of the product. You may need to use other drawings such as Newman projections or chair conformations to reason why you came up with the products that you did. (4 points) IV. Draw the products and name them. If there is more than one product, identify the product that you would expect more of and the product you expect less of and why. (5 points) NaOCH3 HOCH3, high T (2S,3R)-2-bromo-3-methylpentane NaOt-Bu t-BuOH trans-(1R,2S)-1-bromo-2-tert-butylcyclohexane

          I. Identify whether the alkyl halide will undergo elimination (E1 or E2), substitution (SN1 or SN2),
or a combination. Explain what led you to your conclusion (3 points)
II. Draw the reaction mechanism (include all curved arrows) and identify 1) the nucleophile and
electrophile in the first step; and 2) each step as one of the four types: Loss of Leaving group,
nucleophilic attack, proton transfer, or rearrangement. If the mechanism is concerted, identify all
reaction types occurring during the concerted step. (4 points)
III. Discuss the regioselectivity and stereochemistry of the product. You may need to use other
drawings such as Newman projections or chair conformations to reason why you came up with
the products that you did. (4 points)
IV. Draw the products and name them. If there is more than one product, identify the product
that you would expect more of and the product you expect less of and why. (5 points)

NaOCH3
HOCH3, high T
(2S,3R)-2-bromo-3-methylpentane

NaOt-Bu
t-BuOH
trans-(1R,2S)-1-bromo-2-tert-butylcyclohexane

I. Identify whether the alkyl halide will undergo elimination (E1 or E2), substitution (SN1 or SN2),
or a combination. Explain what led you to your conclusion (3 points)
II. Draw the reaction mechanism (include all curved arrows) and identify 1) the nucleophile and
electrophile in the first step; and 2) each step as one of the four types: Loss of Leaving group,
nucleophilic attack, proton transfer, or rearrangement. If the mechanism is concerted, identify all
reaction types occurring during the concerted step. (4 points)
III. Discuss the regioselectivity and stereochemistry of the product. You may need to use other
drawings such as Newman projections or chair conformations to reason why you came up with
the products that you did. (4 points)
IV. Draw the products and name them. If there is more than one product, identify the product
that you would expect more of and the product you expect less of and why. (5 points)

NaOCH3
HOCH3, high T
(2S,3R)-2-bromo-3-methylpentane

NaOt-Bu
t-BuOH
trans-(1R,2S)-1-bromo-2-tert-butylcyclohexane

Added by Lacey N.

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