02Exam3 - Name_ (Last) (First) CHEM 61 HOUR EXAM III...

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Name___________________________________ (Last) (First) CHEM 61 HOUR EXAM III November 25, 2002 Please answer all questions succinctly in the space provided . (8) 1. Draw bond–line structures for the following substances: 2-propyn-1-ol trans -2,3-dimethyloxirane OH O H 3 C H H CH 3 O = (12) 2. Write the mechanism for the ionic addition of 1 equivalent of HBr to 1–hexyne. Show the structures of the mechanistic intermediate and the product and use arrows to show the flow of electrons . C 4 H 9 C CH C 4 H 9 C C H H Br + H Br C CH 2 C 4 H 9 Br (mechanistic intermediate) (product) (12) 3. Outline a synthesis of ( E )–2,3–dichloro–2–butene from 1–propyne. Indicate the reagents needed for each step and the structure of the synthetic intermediate. H 3 CC CH (synthetic intermediate) 1. NaNH 2 /NH 3 ( l ) 2. CH 3 Br Cl H 3 C Cl CH 3 H 3 CC CCH 3 Cl 2
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(24) 4. Fill in the starting material or principal product of each of the following reactions, indicating stereochemistry of the product where appropriate
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This note was uploaded on 02/10/2010 for the course CHEM 261 taught by Professor Kropp during the Spring '10 term at University of North Carolina Wilmington.

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02Exam3 - Name_ (Last) (First) CHEM 61 HOUR EXAM III...

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