Chem 118B Nambiar Midterm 2 Key

Chem 118B Nambiar Midterm 2 Key - 6% 1a \\> Chem 113 B...

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Unformatted text preview: 6% 1a \\> Chem 113 B 7, -// Winter 2011 Second Midterm February 25, 2011 Instructoerambiar This exam contains five pages and five 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: l. (32 pts). Draw the structure of the expected organic product (3) 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. CH3-CECH HBr I g 3 (“ft We fix 4A2 ,3; 92 .\ 1. NaNHz ,1 (97 ,3 (ca/5%; 2. C6H5—CHBr-CHzBr 4, 61" g "’ " M“ 2. CH3I f Mg/Diethyl ether m, fl .3. Hc;c@_{l ______, @4 :16 n», é)(,./ \. _/ 4. CH3COONa + R-CECH ___' ffifl’s > RCl/ AlCl3 a 5. 64%; , , H3 1.RCECLi / g C”) A 6‘ ————* J '-‘ ‘ i _o 2. LiOH OH 1.Br2 7 ' ———————" . @ 2.NaOH 43‘ 1. RQBH 2. H202 / NaOH 9%) i _ ~53} CW.) 8. C6H5—CECH ., *1“ 0 M) 3. (CH3CO)2O/ AlCl3 Lg II (20 pts) Show detailed reaction mechanism for the following, showing the structure of the expected products. 1 . A» a «$4 4" maze/J Dew-reg J29” ~47 fl 7 a???) . 4AM W”? fl + + H0? a 3 COCH3 HNO3/H2504 2' g y ea / ___,, H a ~;,/t«"¢() Hf Jkflkfla ‘ a H (9‘0 6‘) k at (a? Q s {OW/3 FM“, ’\ A/zfl ‘”” " 542/5 v ye) RCOCl (1 mole eq)/ AlCl3 III. (24 pts). Show how you would carry out the following transformations showing the reagents you would use in each step and the structure of the intermediate products formed after each reaction. 1. R-CHZCHon ‘ I, R—COCH3 “5904/{3 N H 5/ 95% 2. Br Br I V. (8 pts) Circle the compounds below that show aromaticity. \ V. (16 pts). An unknown compound A (C12HI5ONBr) has the proton NMR shown below. IR spectrum showed a strong absorption bands at 1650 and 1700 cm'l. 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 Nambiar Midterm 2 Key - 6% 1a \\> Chem 113 B...

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