exam%202%20grading%20key%2008Mar13

exam%202%20grading%20key%2008Mar13 - Spring 2008, 4:122...

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Unformatted text preview: Spring 2008, 4:122 Exam 2 page 1 of4 l4an 1) Draw the indicated structure, being careful to follow the instructions [5 pts each] a) NADH is a biochemical reducing agent. It delivers the equivalent of hydride. Draw the partial structure of NADH using the template at far right. NAD+ is the form of the structure after ! hydride has been transferred. Partial structure of NAD‘ O HQNJ / ‘ \ N I429 sugar— Complete the structure of NADH using this template: oHp. i b) Show the formation of the electrophile for F riedel-Crafts alkylation using 1-chloroethane. (Don‘t show addition of the etectrophile to a benzene, just its formation.) cits Celt” 6:???“ “L3 L (9 %%~*&“Rl% Mmfigm 5%qu (than) mow summit, é’ <11? PH “‘2’ W»; c) Show ONE resonance structure that most clearly 7 demonstrates why ortho-para products are e DISFAVORED when an electrophile E‘ adds to O\ .50 W ,1 nitrobenzene. Use theéeanplate atéight. @N H 567' — 2. 19% l mo H.— d) Show ONE resonance structure that most ('Z/v _ clearly demonstrates why ortho-para products are FAVORED when an electrophile E+ adds to phenol (7L @ l H (hydroxybenzene). Use the template at right 0 Hf {0 (4’ {SM , agswwée E i W/ 0 H */ 6 0L W Spring 2008, 4:122 Exam 2 page 2 of 4 Name m i 2) List the structures in the order of the property requested. Place the letter for the corresponding structure in the space. Least, first; greatest, last. [3 pts each] ‘ a) Wagmmwgwewgl— l C] II II II § l 15 < 9 < HOCHgCOfl H3CCH2c05 FCHZCOE i A B C b) Acidity Wm M O cm:ng chCHQOfl A 8 ll CH3CO§ c llbe Em {WW MAD-top A OH No2 c) Basicity W mfg.) o I 'Il ll Pl < '3 < O CFglCO‘ CHgCO' (CH3)3CCO' — — — A B C d) BaSiCity CH EO‘ HO' WCH O‘ C Q H 3 3 2 , (A < 3 < C/ A B C My e) Reactivity toward electrophilic (H5 in E CH3 CH3 CH3 aromatic substitution ,/ W?” B < O < R M B C H 4%? 1,1,8 . f) Reactivity toward LAH (lithium aluminum hydride) 1905” "F 219461“ ('3‘ a) A (/ CH3CH=CH2 CH3COCH3 CH3CH _ < i < _ A B c g) Reactivity toward H2, Pd [C] MW W Q go cha 2 Spring 2008, 4:122 Exam 2 page 3 of 4 Name z 3) Draw the missing structures or reagents, use letters or write them out. [‘Lpts each] CH CH3 ' 3 55 SD. ay NaBH4- I ’ peroxide CH30H 23’ 0 . W / )W 0/ UK/\ m a? m ‘0 (,9 of; “£3 “1&3 24 WE” : q)» : I ———r ML; (8354 ”?>~ Wm?” Br 0 ('5 n 0 W OH E: « ii —'“ 00ch3 9°”, 602043 (52:13:? COQCH3 5/ W ch0 V “i0 CHgBr‘ Mow. COQH (2 equw) IT ~— _ CH30H \/ W —" i “i' “r w t—i— KER/(E Spring 2008, 4:122 Exam 2 page 4 of 4 Name 4) Show the complete mechanism for the indicated reaction including (a) formation of the Grignard reagent; (b) addition of the Grignard to the carbonyl; (c) quenching with water (and the final product) [9 pts} 0 1) CchHZMgBr. ll CHBCCHQCHg ether 2) H30* . a) my aka/g»): "Ma? C’s/L3 W73 49 C) 09 We obl— €%1k OH H ‘ r. (Er/L7H”? \ (W5 “3:53 ’1 “‘3? “We we CW " 5) Draw the requested structure or list of features. [4 pts each] a) An example of a detergent. Draw the structure AND label the parts. ‘ M W l , 90 v“ QM W _ M; n W 3 b) An example of a prostaglandin (either a genelfiil structure or list of 4 structural featuEesl G35” amme 2 0% W Go ...
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exam%202%20grading%20key%2008Mar13 - Spring 2008, 4:122...

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