140C Midterm 2 V2 KEY

140C Midterm 2 V2 KEY - Chem140C Spring 2008 Midterm 2 Part...

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Chem140C – Spring, 2008 Midterm 2, Part A, Version 1, KEY 1. (25 points) Write the reagents necessary to do each reaction in the box above the arrows. You don t need to specify a solvent unless it is crucial to the reaction. O OH N 3 O NH 2 O OH N 3 O N 3 O N 3 O NH 2 NaN 3 H 2 O/MeOH Br base (such as NaH or NEt 3 reducing agent such as LiAlH 4 or PPh 3 /H 2 O 1) excess MeI, K 2 CO 3 , H 2 O 2) AgO, H 2 O, heat Hofmann elimination gives less hindered alkene
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Chem140C – Spring, 2008 Midterm 2, Part A, Version 1, KEY Page 2 of 6 2. (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 NH 2 H 2 N HN HN HN HN O NH 2 O H 2 N (b) (TWO products) derived from problem 21-17 (p. 978) H N Et O Me O H Me HCl N N N Et Me O Me N Et Me CHO Et Me O Me CHO Et Me O Me N H Et
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Chem140C – Spring, 2008 Midterm 2, Part A, Version 1, KEY Page 3 of 6 3. (20 points) (a) Circle the TWO products most likely to be formed. (The pre-catalyst reacts with base to form the actual catalyst.) N S R H OH O OH
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