322bf03_e2_key

322bf03_e2_key - Fall 2003 Organic Chemistry 322bL C ‘ K Exam 2 “DA “i Name initial of Last Name E(c T.A.’s Name “*0an ‘1 W mama-r:r

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Unformatted text preview: Fall 2003 Organic Chemistry 322bL C ‘ K October 13, 2003 Exam 2 “DA \ “i Name initial of Last Name E (c T.A.’s Name “*0an ‘1. \ W\ mama-r :r m [W MW M Write the products of the following reactions: Assume normal aqueous work-up. (44 pts.) o o CLLgcrg | I ‘ a. Ph-CHz—C-CfH-o-OH [CO ] ($1;me C'rl A 7— r CH2-CH3 COM 0 £ b_ CH3-N=C=O + Hcla o ’ (NMCME — / \ I \‘ g>\/ / O N + H3 (1: Q ~ waH +C0L CH-CH2NH—fi-O-CH2—© —:§——’ 0/ H CL L 3 d. O O CH3 j. Ph-CH=CH-C-Ph I? HCN, EtOH cat. base large excess C—CH3 ————> CI2 and NaOH 0 Qfigw + ems 6L. 1 “(4, MM") if f? OC—Cl + LiA|H[O-C(CH3)3]3 ©/C“H O. ‘ NO 07} 2 R . D p. 00-0. (CHSCHQQCuLi GEM GLUE Et20 -78°C 0 C) R Hoe \C/ q ORH + HO/\/OH __3__> -/ \H . p f t. Ph—E—H _* Ph—CHg‘E-OB ———»NaOE‘ a: M OEt Li 1 A 24 O \ ' . u. ©2KH + BrCszcoZEt 2n (jaw, Cé’ngOLLQE . W A o O O C"[ j ‘OOH H r. V_ ©/lkCHg-CH3 C/VQVCWQ KO \ / 2. CH30—<_=_>’E>‘)-CH3 + CH3—CH=PPh3—> (“j/£0» *CZCW“CV€ @ Name this reaction. fi fSS—CH = P|=>h3 is called an “Ag . (12 pts.) / r}. O’qur , phenol \ I / I, , and any reagents you need; 3. Given acetic acid CH3-COZH ' \ / O-CHz—CozH prepare 2,4-D Q (12 PtS-) C CI 0 4. Write the products of this reaction. Write a kinetic rate expression for this reaction. Write the structure of any intermediates involved. (10 pts.) k ‘ (— g. 0 (A p \ Q 18 I (EH3 0= 0 C? O E_.> __H H20 MAO O [5 W i Meridit© If) msuimiiof f“ 0% it s @ Write the product of this reaction. The rates of theratalyzed reactions of this optically 1 active ketone with Br 2 and Cl2 are {LVQ/ > . The rates of the reactions l l) [ fig; M and _______ but . The intermediate(s) involved depend on the concentration of _ not on the concentration of (12 pts.) 6. Given acetic acid and benzoic acid and any inorganic or organic reagent you need, if ii prepare the mixed anhydride CH3—C-O-C—© The chemical reactivity of anhydrides is comparable to that of gawk Q C\«\O\/‘\ (10 pts.) 9mm (3669 {? CfiCYW‘“—J(M;CT)N®‘ 0 god“ L \ r 1 ©ch {(733 £}C”q WVQr-. O D or; ~® r- ...
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This note was uploaded on 03/02/2008 for the course CHEM 322BL taught by Professor Singer during the Fall '07 term at USC.

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322bf03_e2_key - Fall 2003 Organic Chemistry 322bL C ‘ K Exam 2 “DA “i Name initial of Last Name E(c T.A.’s Name “*0an ‘1 W mama-r:r

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