Chem 143B Winter 07 Final

Chem 143B Winter 07 Final - Chemistry 143B Winter 2007...

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Chemistry 143B Winter, 2007 FINAL EXAM (3-19-07) Total Points: 200 NAME: Ima Key TA NAME: . USE INK FOR RECORDING ANSWERS 1. (12 points) Identify a compound from the list below which contains the following functional group: Secondary alcohol 13 Alkyne 18 Aldehyde 16 Ester 19 Primary amide 6 or 12 Anhydride 1 Phenol 9 Nitrile 10 Sulfonamide 11 Sulfonyl chloride 2 Acyl halide 4 Ether 17
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Et O Et O O OH O O Cl H 3 C O CH 3 O H H 3 C OCH 2 CH 3 O N H O CH 3 OH OH C N H 3 C NH 2 H 3 C CH 3 CH 3 S O O NH 2 SO 2 Cl O OH N H O NH 2 (1) (2) (3) (4) (5) (6) (7) (8) (9) (10) (11) (12) (13) (14) (15) (16) (17) (18) (19) Br O NH 2 2. (14 points) Identify the prominent reactivity of the functional groups present in the compounds below as one of the following (write letter under structure): (A): Acid (B): Base (C): Electrophile (D): Nucleophile OH H 3 C OCH 2 CH 3 O H N SO 3 H Cl O Cl N Et Et Et B D C B D A C
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A mechanistic interpretation of the acid-catalyzed hydrolysis of acetanilide is depicted below: Ph N H CH 3 O H+ H 3 O + Ph NH 2 CH 3 +O HO H CH 3 O HO Ph N H+ CH 3 OH Ph N H 2 + CH 3 OH OH OH 2 Ph N H CH 3 OH OH 2 + Ph N H CH 3 OH OH + H + + H + (step 2) 3. (4 points) The acid catalyst has the following effect on the reaction: A. Lowers the energy of the starting material B. Lowers the energy of the product C. Lowers the activation energy D. Causes the reaction to be reversable 4.
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Chem 143B Winter 07 Final - Chemistry 143B Winter 2007...

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