Chapter 9: Q74P (page 451)
Rank the following species in each set from best nucleophile to poorest nucleophile.

Short Answer




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Chapter 9: Q74P (page 451)
Rank the following species in each set from best nucleophile to poorest nucleophile.





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Why do cis-1-bromo-2-ethylcyclohexane and trans-1-bromo-2-ethylcyclohexane form different major products when they undergo an E2 reaction?
You were told in Section 7.11 that is best to use a methyl halide or a primary alkyl halide for the reaction of an acetylide ion with an alkyl halide. Explain why this is so.
Draw the substitution products for each of the following reactions; if the products can exist as stereoisomers, show what stereoisomers are obtained:
a. ( R )-2-bromopentane + CH3O-
b. ( R )-3-bromo-3-methylheptane + CH3OH
c. benzyl chloride + CH3CH2OH
d. allyl chloride + CH3OH
e. 1-bromo-2-butene + CH3O-
f. 1-bromo-2-butene + CH3OH
a. Explain why the reaction of an alkyl halide with ammonia gives a low yield of primary amine.
b. Explain why a much better yield of primary amine is obtained from the reaction of an alkyl halide with an azide ion (-N3), followed by catalytic hydrogenation. (Hint: An alkyl azide is not nucleophilic.)

Draw the structure of DDE.
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