Chapter 11: Q 11-11-42 E-d (page 350)
Which reactant in each of the following pairs is more nucleophilic? Explain.
d) (CH3)3P or (CH3)3N
Short Answer
(CH3)3P
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Chapter 11: Q 11-11-42 E-d (page 350)
Which reactant in each of the following pairs is more nucleophilic? Explain.
d) (CH3)3P or (CH3)3N
(CH3)3P
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Question: Propose structures for compounds that fit the following descriptions:
(d) An alcohol that reacts rapidly with HCl at 0 °C
Draw the structure and assign Z or E stereochemistry to the product you expect from E2 reaction of the following molecule with NaOH (green = Cl):

SN2 reactions take place with inversion of configuration, andSN1 reactions take place with racemization. The following substitution reaction, however, occurs with complete retention of configuration. Propose a mechanism.
.

Question: Arrange the carbocations below in order of increasing stability.
a.

Reaction of iodoethane withyields a small amount of isonitrile,, along with the nitrileas the major product. Write electron-dot structures for both products, assign formal charges as necessary, and propose mechanisms to account for their formation.
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