ezam 3 eky - EXAM 3 V NAME K{73 1 Give the IUPAC name for...

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Unformatted text preview: EXAM 3 V * NAME K {73/ 1. Give the IUPAC name for each of the following compounds (20 pt) '1 C' CH3 l ‘ ' .. — :c—CH a) CHgCHBrCCIC(CH3)2 (1:143 (‘,q C; L . x ‘5'” +vZ—ene. b) 4—}Mmo—3'ckloro— z-nan “d ' PM 4- ‘xzromoc‘dcJ °”‘e P+e me. ,9) II. In each of the following pairs of reactions, predict which will probably be the faster reaction and indicate the dominant mechanistic pathway (8N1, SN2, E1, E2) of that faster reaction. Explain your answer for full credit. (15 Pt) A) CH3CHZCH(CH3)Cl + ._CH3OH ———>CH30H20H(CH3)OCH3 +_ HCI vs. N ‘ CH3CHZC(CH3)ZCI +'-CH30H ————> CH3CH2C(CH3)2OCH3 + HCl Suit 3' Carbocmo'n is more stable. W 2° Carbocdd'lom. wear/(thaw!— B) (CH3)3CBr + N03- -—> (CH3)zc=CH2 + HNO3 + BT- WW ‘ (CH3)3CBr + NHZ' ———> (CH3)ZC=CH2 + NH3 + Br' ’52: +hc rxm will .9» Quick WH’h a sl'rmxfilr loci/M, C) (CH3CH2)ZCHCH20TS + CsOCH3 9 (CHgCHz)ZCHCHZOCH3 VS. (CH3CH2)3CCH20TS + CSOCH3 9 (CHSCHZ)BCCH200H3 3N2; mm {,0 [£38 $+€Vic hindramu pm, ~+lxxn First V‘anhM III. Predict the major organic product(s) for each of the following reactions. Show the stereochemistry of the product when it is pertinent. (77 pt) A) H CH3 Cl . , . fl C?H3 + Nai3r —-——> ‘0‘ SNL 5r H V . 'mvtVSWV‘ H H CH3 06) 9 H2504 d B) _————————> » CH: #9” C145 H H H -9 u G J ) 1) BH3-THF 2) H202, NaOH OCH'LC‘a 3 H 1) Hg(OAc)2, CH3CH20H \ 2) NaBH4, NaOH , 3 H IV. Write a mechanism to explain the product formed in the following reaction. Show all steps, formal charges, appropriate curved arrow notation, important resonance structure, etc., to receive full credit. (20 pt) OH THS l 7‘” CH - H SO “—""" _ C/ \CHZCH3 + 2 4 . [:>=c Ci 1 K , CH2‘CH3 H \ O C H t ’H ,Hap CH3 CH, 0m [I 1 ‘5 ___;; ‘ cw“ l l - .4, -H .___.c —-— 4 C ‘— Q\c——c- "'40 u o 3 0": l I Q’- 0— l l o G q at E { 2* I’LW ski“ CH3 _ W H 0343 IV. Give possible organic compound structure(s) or reagent(s) indicated in each box below. (18 pt) reagent(s) B? HCl Product(s)? ...
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