Exam_2-Key - 1. (6 pts) Give the degrees of unsaulration in...

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Unformatted text preview: 1. (6 pts) Give the degrees of unsaulration in the following molecules. 0 of H Br I / t I HO Br NC F30 a 2. (6 pts) Rank the following compounds in terms of acidity. (1: most acidic) F30 /— I‘. '— { I H3C 3 .L :4 due wt 5 f 3. (6 pts) Rank the following alkenes in terms of their relative stability. (1: most stable) Sfifi each 4. (25 pts) Fill in the boxes with the appropriate starting material or product(s). cozH Small amount of large excess (CH3)3COvOC(CH3)3 5. (15 pts) Provide a detailed curved arrow mechanism for the following reaction. The stereocenters are not defined. In your mechanism propose stereochemistry for one of the enantiomeric products. O .' 0/03/7027 0 —'——> n OJ 1. CH3CCNa / + 6/ -‘ 5/95"?”MM ’0 2. BI'2 Br +3 xix :C—CFES affereaéflll‘filx’y *3 5 mm! (#476 i, fife/f” e 73—?er 0 o J \ \ d x "—7 f [/1 Infr/ I; ‘9 < i ? Br 6 q V “(E-6" 0H ‘3‘ + \6 3-13.“ > \ \ Doom 7 #- firm/r \ ,sr ”' 11 \ I59 U" ére' Br 7. (21 pts) Give the reagents to carry out the f0110wing reactions. 1-H FM MCPEA— Cmdifims, -2 {IV Pia/I‘qu ‘mcomok H Q 8. (13 pts) Provide the best synthesis for (3R,4R)-3-ethyl-4-hydroxyhexanal using any combination of the organic compounds in the box and any of the reagents discussed thus far in 5.12 (the reagent can only contribute non-carbon atoms to the final product). Be sure to show how you would prepare each intermediate. If". r *' OH O (3R,4R)-3—ethyl—4-hydroxyhexana1 2 KO“)! “90% [Leg o’efieu V ‘t- 2 Nguug "L I A . \ H \s «E Extra Credit (3 pts) Draw a detailed curved arrow mechanism for the reaction of mCPBA with ethylene. r 4‘6.» .__, \ /\ ghee“ ‘ H +21% \L “Camd— 0. i0 ,5 3 H "" CDnrd mech‘mgh C(' —q ...
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This note was uploaded on 02/14/2012 for the course CHEMISTRY 5.12 taught by Professor Saraho'connor during the Fall '09 term at MIT.

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Exam_2-Key - 1. (6 pts) Give the degrees of unsaulration in...

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