310MReviewProblemsKey - CH 310N Dr. Brian M. Bocknack...

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CH 310N Dr. Brian M. Bocknack Spring 2007 1 Review Problem Set – Answer Key 1. Write the structure of the major organic product formed in each of the reactions below. Be sure to indicate stereochemistry clearly where appropriate. If there is no reaction, write “N.R.” as your answer. (a) H 2 SO 4 (cat.) H 2 O HO (b) CH 3 OH (CH 3 ) 3 C Br + Na OCH 3 (c) CH 3 OH + Na OCH 3 O OH OCH 3 and OH OCH 3 (d) CH 3 CH 2 C CCH 2 CH 3 H-Br (excess) Br Br (e) H-I (excess) CH 3 CH 2 CH 2 OCH 2 CH 3 I + I (f) CH 3 CH CH CH 2 CH 3 + HCl + Cl Cl major (due to carbocation rearrangement) (g) Cl 2 , H 2 O OH Cl and Cl OH (h) CH 3 OH + HCl Cl CH 3
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(h) 1) OsO 4 2) NaHSO 3 , H 2 O OH OH and OH OH (j) 1) O 3 2) (CH 3 ) 2 S O H O (k) I + CH 3 C O O Na DMF O O (l) 1) BH 3 2) NaOH, H 2 O 2 , H 2 O OH H and OH H (m) CH 3 C CH CH 3 CH 3 CH 3 OH + HBr H 3 C CH 3 CH 3 Br H 3 C + H 3 C CH 3 CH 3 H 3 C Br major (due to carbocation rearrangement) (n) CH 3 CH 2 CHCH 3 OH H 2 CrO 4 O 2. Provide appropriate short answers for each of the following questions. (a) In each pair, which is the stronger
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310MReviewProblemsKey - CH 310N Dr. Brian M. Bocknack...

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