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key_Test_4_CHM_2210_Summer_2013 - Test 4(Summer 2013 1(25...

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Unformatted text preview: Test 4 (Summer 2013) 1. (25 points)(Includes 0.5 points for each correct name) Identify the products of these reactions (One bonus point for each mechanism. In some instances, a partial mechanism, as done in class, is required for bonus point). Show stereochemistry, where appropriate. If more than one organic product is formed, just name one of them. /, ,f H + / L», o H (3 E ,_ , ,. fl/ \ . avg/fl Name: WW (. damn/M639 # '5 w fl‘QAQ/AGL r ,sz i [H i I, J v, 1. 0804 , H202 2. mannitol Vi : i / Name: 2 ‘5 ~ avocaigg; :I ~ wmafioacflyo ()(wef w 1. m—CPBA 2- H20, OH- / X J Name: \ 2 2 “' Ub'gflaflcij (fldpa/M’flma 0 H ,/ v“? 2 ,z ‘ 3} , f E Br H20 OH- heat Br 0y 7 /" 6‘” w {by 1, BH3 j I’ll 0"; ff; 2. H202 OH— / f \ x/ Mg] 5‘ Name: l,“ "’(KAI/3::”RI-1,014.4fiery/Vtav’ié/mzv/ ’ [7 (2‘ V’ Name: ("a M 2 ”’7“ "6‘ Am. wage“ (4 - myvxww zV/g/ r1 Name: ’1 \ J [- 2. (15 points) How would you do the following conversion? Show ALL intermediates. (More than one step may be required). \ > Br Br //\ /\ /\ V ,/ \ / \ _, S r“ , 1‘; j / ( \ W \\ 1 l(/ "‘ )1 /\ / x G ill \77 y 3. (15 points) Consider the following reaction. a) This reaction leads to two different ketones. Suggest mechanisms for the formation of the products. ll /\\ ,,,, D-CEC‘O ——*H202’+H+ \i ?‘ {WI it ’7 QM é“w<\ Hg “Wu/f"! ”.1" 4. (10 points) Identify the following compound (C3H1602) using the 1HNMR spectrum shown below and assign the peaks (hr = broad) : ’C/HB [£74 (”M3 ”(ML 0 H 44' H 0x ll b‘ j A { curbwomowc; x Q’s I A / CC H s (l Hq’ 0/” /// X 5. (10 points) Identify the following compound (C13H1802) using the 1HNlVIR spectrum shown below and assign the peaks (br = broad): ,,.’ 6. (10 points) Draw structures of at least®compounds that would fit the information presented below. Write down the IR bands that support your case (just mark the relevant peaks on the spectrum). Molecular formula = C6H13NO. [DD E50 , n anon 5060 200:: mm mm] ..| lfilltl moo suo L ”g: (A!) i, I) ,1 “l \(3 E) g: .2 2, \ l l l l l7 i 4 Vi i 1 l I \ N / \/'///\\V‘~ I / 0 / 7. (15 points) Identify compounds or reagents A, B, C, D and E. OH m.» A + B + C 1. 32% 2. NaOH, WOZ ...
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