Midterm_2_partA_V2_KEY

Midterm_2_partA_V2_KEY - Chem140C Spring, 2008 Midterm 2,...

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Chem140C – Spring, 2008 Midterm 2, Part A, Version 2, KEY 1. (15 points) Circle the most likely product. (a) Cl Cl 1) NaCN, H 2 O, base 2) excess LiAlH 4 , Et 2 O 3) acidic workup CO 2 H HO 2 C HN HN HN HN O NH 2 O H 2 N NH 2 H 2 N (b) (TWO products) H N Et O Me O H Me HCl N N Et Me CHO Me CHO Et Me O Me N H Et N N Et Me O Me Et Me O 2. (20 points) (a) Circle the TWO products most likely to be formed. (The pre-catalyst reacts with base to form the actual catalyst.) OH O OH OH HO OH O OH OH OH HO OH N S R H OH Cl (pre-catalyst) base H 2 O HO O H OH HO HO H HO H O OH HO O HO OH O OH H O
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Chem140C – Spring, 2008 Midterm 2, Part A, Version 2, KEY Page 2 of 6 Here ! s the mechanism, just like other thiazolium reactions discussed in the book and in class: N S R H Cl base N S R R' O H R' = OH HO R' OH H S N R Base R' OH S N R R' O H enamine attack, followed by proton transfer R' O S N R R' OH N S R O R' R' OH O OH OH OH HO OH both are acceptable answers O OH HO HO HO OH (b) The other reactivity is base-catalyzed aldol (we had a very similar question on the
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This note was uploaded on 06/07/2008 for the course CHEM 140C taught by Professor Nefzi during the Spring '06 term at UCSD.

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Midterm_2_partA_V2_KEY - Chem140C Spring, 2008 Midterm 2,...

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