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Chem 317 - Exam 2 key

Chem 317 - Exam 2 key - CHEMISTRY 317 WINTER 2008 EXAM II...

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Unformatted text preview: CHEMISTRY 317- WINTER 2008 EXAM II - Thursday, February 28th NAME: K E I (last) (first) 1. This exam consists of 5 questions. Do the ones you know how to do first, then come back to the others if you have time. 2. Please, do your own work! QUESTION VALUE TOTAL 100 — -- -- -— - MAKE SURE YOUR EXAM HAS 8 DIFFERENT PAGES INCLUDING THE COVER SCORE 36 - 36 - 0 _ Some Common IR 5 C C _—~17oo Name: 5 Y 1. Circle the correct response for each of the following: (3 ea) a) Which of the following is expected to be the-most reactive? [ :0 jk/ E : <1 O b) Which of the following is expected to have the highest boiling point? JOH/ . (1/ ”Er /§/ c) Which of the following is expected to give a positive Tollen's test? Circle all that apply. d) Which o the following is expected to be the strongest base? 9 N/ O UNI-'2 O / e) Which of the following is a secondary amine? 9% Av . Q/ f f) Which of the following would be the best solvent for a motion involving CH3Li? l ,2—di methoxyethane ethanol propanal water acetic acid .- Name: 5 g) How many equivalents of CH3MgBr would be consumed by the compound shown below: 0 K 0 .r "' 2 CH3MgBr s CH3MgBr Z ( 0H 3 CH3MgBr 6 CH3MgBr 0 o o \ 4 CH3MgBr more than 6 CH3MgBr 0 N “Hz h) Circle the imine in the structure shown to the right: 1) Which of the following often serves as a way to protect alcohols? reaction with reaction with reaction with Na cover the 0H none of these t-BuOI-Ilacrd HOCHZCI-IZOHIH" with duct tape will protect an alcohol Name: K E \ 2. Complete each of the reactions below. If no reaction occurs, write ’no reaction’: a) b) C) \ 2) NaBH4 ~ H+, excess H20 0 d) (V H z 1) n-BuLi S 2) X/ e) </ Br 8 3) H+,HgC12,H20 W O OH ' o 1) 2 CH3CH2Li 2) H20, H+ g) \ \ 1) N HZNH2 g -—--—_—> 0 h) 0 2) NaOH, heat 0Q o D \jk/ 0 j) \/“\/ o 1)KOH NH 2) Arms ApNHz k) --———-—> 3) NHZNHZ, heat \ O 1) SiazBH H —-—————-> D 3‘71 2) H202, NaOH Name: K E t 3. Using correct arrow formalism, show the correct mechanisms for each of the ( 6M5 60v) following transformations: X H+, H20 k ——-—-——-—> a) O/\ /\OH + \u 3V” fl°]/ l4 A u? of <2— 6‘) 4' AOH I H 14- :H .4 H + «9” S A; H”; (“9 name 0s : Jo» w». _./J tr KEY Name: 4. Devise a synthesis for each of the following. You need only show 5 b 65:) reagents/ conditions etc. . .. No mechanisms are required. L F i’ a) start with and make W “32) and any other reagents you need «4 b 0 [big/VD” '0 0’) 0 l \O/ '2’; WI ,3, ~o /5—— W '4‘ t ° , ‘b e,»— 3 O / b) start with O and make 0 l Ht 0 Pet 0 \ 1&0 [3; M 0H "’2 N o Name: JEL 5. Explain carefully (use a mechanism to aid in your discussion) why an acetal can’t be formed using the following reagents. (2 LT excess /\0Na Ff; —___, NOACETAL! inethanol H“ /\o— co 0v . AX 540? W N 0/\ ,s a show] EM, awi’ ai/ac/CS 74x4 [9 when. , cm, W ~ “a,“ T0 muff/wt 7L0 an zap/'51) a, hen/n— . , \ jam—00: mz/Jf 13L 00/1ka 5/1"? a 5006/ lea/'45 yet/fl m0 3; AMP“ ,‘A [94‘9“ I; may]: 2/: 74% Arm I . cm ~ 0H ov‘ (M 6M W/ AR” ) ...
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