midterm1key

midterm1key - Chem 118 C Summer Session I 2008 First...

Info iconThis preview shows pages 1–8. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 6
Background image of page 7

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 8
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Chem 118 C Summer Session I 2008 First Midterm July 8, 2008 Instructor : Nambiar nd six problems. Please make sure that your copy This exam contains eight pages a please let us know before you start contains all the eight pages. If there is a problem, answering. Please answer all questions. l. r30 pts‘). Draw the structure of the expected organic product(s) 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". Q r) R—CN 1.H+/H20/A v _0_QZ+ — J ___.__.____—._eiv 2. CH3OH / H+/A CH OH/OOC __._ 2‘) CHg—CO-Br 3 C HJ/ (E 0% M A] M Z A / x0 ,/OY:\/YOH CH3Li (1 equivalent) F 2) 4; Ho—JTEHCOOH CHBMVB a gay +852 U) 1. R Mg Br 5‘ CH30—CO-O CH3 2. H+ / H20 J 1.RLi iHSCd§——({ 1. 6: C6H5-COOH p 2.H+/H20 b 0 _, ,0 H NHzOl-l 1‘ ,A/HwH + a 7) (R-CO)2O ________> ~ @ ">9 1. [(CH3)2CH—CH2]2AlH/—780C _ __ "r 8) CH3CONHC2H5 C2 é H .f 2.H+/H20 (/02 H5”4l/H\i 1. LiAlH4 9) C6H5-CONHCH3 % [7(5- GHJf/VF'Gfiég 1., @géiO/J 2. (CH3CO)20 /66% d a 10) CH3COO N02 CH _£ 7 ,/ ,1 A! ‘ ' d M "‘U + 457 NH /A g _, f {1/ A“ Ila (10 p15) Show detailed reaction mechanism for the following showing the structure of the expected products. I] '3. (10 p15) Show detailed reaction mechanism for the following, ‘HOH Ill (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 products formed after each a step. ' ‘ l . COOCH3 CHQCOOK ,0 “r” W W / N 6/ ‘ p Hay" 0 RCOQCH3 RNHCHQCH2CH2CH29H Hat [1/de wag? W 2 a?) u 41/ H \ V . m <31 ,n/QL’EEW H Afik p fl\ a i/ “(9H fl , My flak (g s. RCOOCH3 RCH2CH2NHCH2’O [1—6 v ' , ,_ I? <3 “ 02 4317b: 4. CH3CH2COOH CH3CH(0H)CH2CH3 J90“ #62144!) M? _ 4(le V a) fit 5 IV. (16 pts) Provide a systematic name or draw the structure as appropriate for the following compounds. 2 ‘ k f 1. CH3$HCH2CHBrCOOH a? — BMW- A_GWW~MO Mme NH2 —-—@——COOCH2Br 63/; 4 CHg-CHCl-CHg-O—COCHg—O 55W N00 ._. L CH3—CH(OCH3)—CO-Br “M r— (7624 5. (Z)—2—Butenoic ethanoic anhydride /\L2/fl"ZF 3 0 WM CHzBrCHzCHQCHQCN 5’9"— er fl W (AW N, (L CH3CH2CH2CH2CONHCH3 V7. N-Methyl— 2—( 4—methoxypheny1) Ethanamjde. \r’ (f [O ptsj) Rank the following compounds in the decreasing order of acidity. CCOH COOH (EOOH COOH OH CH3CH20H f - © @ @ £31 5) i a 5 CH; N02 CH3 A B C D E F OK CONHCH3 ONa SOQOH ? E o E 5 Q (a: V G H I J \1 V l. (20 pts). An unknown compound A (C9H16NO4Br) gave the proton NMR spectrum shown below. Deduce the structure of compound A. What would you expect to get when compound A is l) reacted with lithium aluminum hydride? 2) NaOH / H20 / A 6H #3; _ five M3 - - 3H .‘3H \ \ 2H fie “ /<i\Gt\\ 1] 5 M i 9 8 7 6 5 4 3 2 1 o Ppm(5 . ‘ ,lux L4; 7 €H~GH”Va—@HQV-€H “3 C? «W344 l 9\ fix (is! J 5W \3 a \3 6 WM; —~CE#~€H& L'AIH 853 (CAL a a: gt; 08 l) CompoundA 4 B d T ‘ : v‘ v «ij 7‘ ch/ompoundA NaOH/H2O/A AGH “é? jy EKCIIFVQ U é, A fllf fl ,/1/&\ ...
View Full Document

Page1 / 8

midterm1key - Chem 118 C Summer Session I 2008 First...

This preview shows document pages 1 - 8. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online