Unformatted text preview: O d.
1. NaNH 2
2. Na, NH 3 O OH 3. H 2O
TosCl, pyridine NaCN
Br CN 4 2. Joe Bob, an 8th year senior taking CH 231 for the fourth time, has proposed to carry
out the following reactions. Most of the reactions will not work as desired, however.
If the proposed reaction would work, write “correct” in the box. If the reaction would
not give the desired product, draw the product that would form. If no reaction would
occur, write NR in the box. Briefly state why the reaction would not work.
H 2O a. OH Br Br OH
In this reaction, the OH is added to the more
substituted carbon. NaC C CH3
Strong base with secondary RX will give E2
product. c. Br NaNH2 NH2 DMF d. 1) BH3
2) NaOH, H2O2 Correct HO H HO H
H H H and OH are added cis. Joe Bob has the wrong
diastereomer of the product. 5...
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- Fall '11
- Organic chemistry, Chemical reaction, Trigraph, Actual Product, Sodium amide