Sample Exam 2 Key - Exam 2 Chemistry 345 (Nelsen) 1. (16...

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Exam 2 Chemistry 345 (Nelsen) __________KEY ____________ (Name: please print) 1. (16 pts). Give the products of the following reactions: (a) (Ph 3 P=O could be one of the products) (b) (c) (Arbuzov reaction) (d) 2. (12 pts) Give an arrow-pushing mechanism for the following reaction: O OH NH 3 + Cl - HO H N Ph H + Cl - I show acid catalyzed opening because it requires fewer arrows, but base would be OK too, and one could go to the cyclic cation first instead of the acyclic one shown. You lost points for S N 2 reactions to make the CN bond. O OH NH 2 Ph H + O H O + H H OH OH + H 2 N Ph H OH HO NH 2 Ph ~H + + H OH H 2 O NHPh + Cl _ acid-cat. acetal opening amine adds to aldehyde dehydration need proper arrows for: 2) hydrolyze (H 3 O + ) Al H O -78 o C, THF Cl O H O P + CH 2 CH 2 CH 3 Ph Ph Ph 1. BuLi 2. Br -- H (two major products) H H H H P O C H 3 C P O O O 3 H H heat CH 2 Br H 2 C O H NaCN H + (less than 1 equivalent) H OH CN (cyanohydrin formation)
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2 3. (12 pts) Circle the carbons in the structure below that are at the carboxylic acid level
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This note was uploaded on 02/14/2011 for the course ORGANIC CH 341 taught by Professor Idk during the Spring '11 term at Wisconsin.

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Sample Exam 2 Key - Exam 2 Chemistry 345 (Nelsen) 1. (16...

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