1aa3-2012-tut10-a

1aa3-2012-tut10-a - CHEMISTRY 1AA3 Week of March 19, 2012...

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CHEMISTRY 1AA3 Week of March 19, 2012 TUTORIAL PROBLEM SET 10 – Solutions ______________________________________________________________________________ Page 1 of 3 1. Fill in the missing reagents a. to f. for the following transformations. O OH O H OH O O a. b. c. d. e. f. SOLUTION: a.: PrOH, H + , heat b. H 3 O + , heat c: KMnO 4 , H + or K 2 Cr 2 O 7 , H + d: 1. NaBH 4 2. H 3 O + e: PCC, CH 2 Cl 2 f. KMnO 4 , H + or K 2 Cr 2 O 7 , H + 2. Complete the following oxidation reactions (if no reaction occurs, write N.R.): SOLUTION: KMnO 4 K 2 Cr 2 O 7 / H 3 O + (i) (ii) OH OH OH PCC CH 2 Cl 2 (iii) (iv) (v) (vi) OH O K 2 Cr 2 O 7 / H 3 O + H O PCC CH 2 Cl 2 PCC CH 2 Cl 2 O N.R. N.R. N.R. O OH O Note that PCC can be used for one 2-electron oxidation step. While it can selectively oxidize a 1° alcohol to an aldehyde (one oxidation step) it can also be used to oxidize a 2° alcohol to a ketone.
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2 3. Identify the nucleophile in the following reactions. SOLUTION:
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1aa3-2012-tut10-a - CHEMISTRY 1AA3 Week of March 19, 2012...

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