Exam_1_Green_Key - gm 6&7 CEM 252-8pringZO11/First...

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Unformatted text preview: gm 6&7 CEM 252-8pringZO11/First Exam ..... (page1) 1. Draw the structure of each of the following compounds. (16 total points) a) p-t—butylaniline b) benzoic acid 0) formic acid e) 2—phenylbutanoic acid f) o-nifrobenzenesulfonic acid - 9) m-chlorophenol 2. (2 pts.) Encircie the correct configuration prefix (A, B, C or D) for the following diene: ‘ ' CH -—CH CH\3 — / 2 fl — /CHQCH3 /C_C\- . /C_C\ H 1 H CH3 1 CH3 (2E, 6E) (2E; 62) (22. 6E) (22, 62) A B C CEM 252 - Spring 2011/First Exam ..... (page 2) (12 points total). 3) a Q ‘B— The above energy diagram is for the reaction: X —-- A + B + C a) Which product (A, B or C) is formed fastest? A 2 Dis b) Which product (A, B or C) is most stable? C) Which is the major product under conditions of -2 pts' kinetic control? d) Which is the major product under conditions of -2 pts' thermodynamic control? 4) Complete the following Diels-Alder reaction: Ilene p 8- Dienophile 2 pts. CH3 CH3 CEM 252 - Spring 2011/First Exam ..... (page 3) (16 points total) . _ A B c D a) Which one of the above trienes (A, B, c or D) 2 PW- has the iowest heat of hydrogenation? A b) Which of the above (A, B, C or D) has the iongest 2 pts‘ Wavelength absorption (highest )t. max) in the UV? -————> a) For the above reaction; draw the two major resonance structures of the carbocation intermediate. 2 pts. carbocation intermediate b) Draw the structure of the 1,2 and the 1,4 addition products of the reaction: 2 pts. 1,2 product 1,4 product C) Which of the above products (1,2 or 1,4) is more stable? (I ,4 2 ms- d) Which of the above products (1,2 or 1,4) is formed faster? (J 1 2 pts- CEM 252 - Spring 2011/First Exam ..... (page 4) (18 points total) 7. Which three of the following compounds (A-H) are expected to be aromatic according to HUckel’s Rule? CH3 H Ill H o l l / H HC:CH H A B c D o H 0 H ,O H H I l :H: :H: I ‘ GH§Q\6/C\C4fiH2 Q H N H 2 'l i. E .L H H H F G 2 pts. I ' 2 pts. ’ 2 pts 8. Encircle the more stable carbocation in the fol-Io’WTnQfi'rrs: b) OCH3 I (2 pts.) 0r CH2 =c—CH2 (+) H0 =CH—CH2 (+) 9. Draw appropriate structures in the boxes: three resonance structures of carbocation intermediate major Organic product CEM 252 - Spring 2011/First Exam.....(page 5) (30 points total) ' 10. Draw the structure of the major organic product: a) © 163% 0(ne equivalent) b) CH2CH2 &, @’ H2804 c) El) CH2C—H CrOs —-- @ H2304 CH20H20H20H3 ' 2 pts. d) @ Brz —- m: e) 2 pts. CH2CHECH3 A ————-—> KMHO4, H20 f) soaH Brz ——b FeBr3 9) N02 2 pts. © HN03, H2304 (excess) h) 2 pts. 2 pts. i) 2 pts. CHZCHZCHg 2 P‘s- MCI—3- CHBCHQCI CEM 252 - Spring 2011/First Exam ..... (page 6) (8 total points) 11. Encircle the side favored at equilibrium in the following acid-base reaction: "ax ICI \ ' (I); CH3CHC02N3 + CH3CH2CO2H # CHQCHCOZH + CH3CH2C02Na mm- 12. (6 pts.) Outline the steps in an efficient synthesis of the following compound starting from benzene: _ No2 ' Make: @ /CH3 From: © CH20H "“ 0 it RW/ HQ 3) Egg/LNG?” \“’\ L ...
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