Chem 118b W 2011 Midterm1 key

Chem 118b W 2011 Midterm1 key - Chem 118 B Winter 201 1...

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Unformatted text preview: Chem 118 B Winter 201 1 First Midterm February 4, 2011 Instructoerambiar This exam contains six pages and six problems. Please make sure that your copy contains all the five pages. If there is a problem, please let us know before you start answering. Please answer all questions. Name: Last First MI I.D.# Lab Section: TA: Problem # Points l [I III IV VI Total l. (32 pts). Draw the structure of the expected organic product (5) formed in the following reactions. Unless mentioned otherwise, you can assume that all reagents are present in excess. If no reaction occurs, write "No Reaction". 1.H+/CH3OH/A ; _ ——-—- m 2.NaOH L3 1. CH3-CH=CH2 2. C6H5-CHBr-CHZBr C? H5 ” J 2. CH3I Mg/ Diethyl ether 3. HOOCI 5/? flak} 4. CH3COONa+ &H (W Br CH3MgBr (lmole equivalent) 5. O—CHzCOOH N3 + 355,}, H3 l.RCOOOH V ,aM 6- ———-r a 2. NaOH/A flfl / CH3 1.112504 ’9 $29 7. OH 2.KMNO4/H20 8. C6H5-CH=CH2 M II (20 pts) Show detailed reaction mechanism for the following, showing the structure of the expected products. 1. eH-r 1.03 2 RCHz- =CH2 .___... Eek/TL 2.(CH3)2S (9 + wagfl 0 + J/ ’31: III. (24 pts). Show how you would carry out the following tran sformations showing the reagents you would use in each step and the structure of the intermediate products formed after each reaction. l. R-CH2CH20H R-C:C “‘\ i WW6 a v @u ¢ 84$ \|/ 6 5") WW “9— awgrefiéy-‘S b ———v 6/ WWW/6 A fly P 7%? 3. _____.. M” \ @‘b “351— 01—6269 1v. (6 pts) Draw the structure or give the name as appropriate in the following cases. OCH3 1. CH3CH2C‘ZH /Cl .. d _ :C=C ‘ l" W -Z r H \Br fl L~W~LZ222Q V - (6 P“) Show the structure of the products formed in the following reactions indicating stereochemistry. Indicate if you expect the product to be optically active. 1. R '3: H H =53H I C03H H(\ I’CH3 Fm“ / Cis-2~Butene —, (c—c + g—(g‘vfl 2. H+/H20/A H 1:: R:\OH HQ: cu, (23,31qu mmuw Mm) VI. (lZpts). An unknown compound A (CngstCl) has the proton NMR shown below. IR spectrum showed a strong absorption band at 1650 cm‘1 . Determine the structure of the compound. ...
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This note was uploaded on 02/21/2012 for the course CHE 118B 118b taught by Professor Many during the Spring '12 term at UC Davis.

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Chem 118b W 2011 Midterm1 key - Chem 118 B Winter 201 1...

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