key exam 3

key exam 3 - kt»! ' Ext-“‘03 2 1. (19 pts) (a) Circle...

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Unformatted text preview: kt»! ' Ext-“‘03 2 1. (19 pts) (a) Circle the group with the higher Cahn lngold Prelog priority in each of the following pairs (6 pts). H30 2) and —CH2—-—~l}l—CH3 CH3 3) ~CH2—CL and Br (b) The sex attractant of the codline moth is the 22, 6E stereoisomer of the molecule below. Write the structure of this substance in a way that clearly shows its stereochemistry. (4 pts). CH3CHzcH2c=CHCHZCH2c=CHCH20H' Quacnguah CH3 CHZCH3 m/ H H C/ M\ 5 (“421% \ 1c i410 H /<'Z\ QHBCl—ll H (0) Provide the lUPAC names for the following compounds. Be sure to designate E or Z stereochemistry for part (i) (6 pts). Baahlvro ~~E a m eihtdt —, ,2 a 1% ~e,thfil .—- lw lgwpropglc Sclbw P701179! so:- ;.;heap+@nw \UGI begging » I '3~‘Q.th3l~ lehnfiflagl'" (d) Draw a structure for the following molecule (3 pts): atMrjl') ojdl o ham“ a 4—methyl-4-penten-2—ol T7“ gill-g I I i I ' ‘ “r.”- I. , 9’6. 10 3 2. (38 pts) Draw the principal organic product expected from each of the following reactions. If more than one product is expected, be sure to indicate which is the major prodUct. Pay particular attention to STEREOCHEMISTRY AND REGIOCHEMISTRY where appropriate. (a) butKS W «a +- ~H % Q “ CH3 K 00(CH3)3, : C443 résfltOCAEm‘lS'Ef‘tj ....,CH3 HOC(CH3)3 , w- :2, Br . (b) Hoc(CH2cozH)2 st04 H \ “C923,; no; u C02H A Dr :i citric acid HGLé QMZ \ (02%} Hmfifiuz \ C191” 0 " r. (c) B CH a” ' T 3 CHscHzo'Na+ /f «e3 roommsgcj ....______.—_—. " - . CHgCHQOH O ' “ 1 (d) HO CN KHSO4 W333 ‘7 Q‘em‘s’t'rfl M' —- ’2, H300 heat . ~ (9) HB ‘ 1 t9}. - i 2-methyl-2—butene "35m eml *3 peroxrdes Br —— 1 (f) we ' s‘» l t“ CH3 r ' “kc/rebgndmlS 13 abs-'3 “2 dj” “‘9 ' " ._.._._.__.__..__, in H Pt Which reaction part above involves a non-Zaitsev elimination? CL ‘ (2 pts) (Q) (h) (i) (i) (k) (1) CH3 8,2 m HCI -------—-—> OE -——————> H20 H20 .—.——.—.’ H2804 CH3 (catalytic CH3 ———-——> CH3 amount) BQHS H202 ---——--———-.' NaOH “‘1 $51.7 may“ m 1.03 .___......_.._...’ 2. (CH3)ZS ' H or O refi}oche,m1§+rj -° 2 SEQreodag-m‘ug‘rrj "‘ K efareocLh am . ....’l res’iochm. “CL .6“? H {refiivchewmlgt 3 110+ cm 3990c», 3 r‘nui'fi: be, 351”) (Adam. 3. (13 pts ) Complete the following questions: (a)The carbocation below has the potential to tearrange to a more stable carbocation. Write the structure of the rearranged carbocation (3 points). 69 (CH3)QCH CH CH3 _ Q) CH3 (b) Draw out the alkenes you would expect to get from the E2 elimination of 2-bromo-2—methylpentane (4 pts). 3PM ‘2 (07$. en- ‘ (c) The reaction of t-butene with bromine, Bra, in aqueous solution gives primarily 1-bromo-2-butanol. Identify the nucleophilic species in the reaction (3 pts). A. Br2 flfi «to. D. HOBr . (d) Which of the following alkenes is expected to have the highest heat of hydrogenation (circle the correct answer (3 pts)? If. 1— entene B. trans-Z-pentene C. cis-2-pentene D. 2—methyl-2—butene 4. (16 pts) (a) (9 pts) Compounds A is an alcohol of molecular formula CGHMO. On being heated with sulfuric acid, a major alkene B and a minor alkene C are formed. Ozonolysis, followed by treatment of the ozonide with dimethylsultide, of major alkene B gives acetone (structure shown). What are the structures of compounds A and B and C. Briefly explain how you arrived at your answer (you can answer this by showing reactions). 0 HgCJLCHa 1 ms, _ acetone - I ‘> ‘ 3 ..~ 0 H [>7r.S )«izge r. '19,» ' A N '2 Pts 2??» Gal)! . C‘ as B c; Q \ U73 V L @372?) >jo ls acetone and aldehyde or ketone? Haemez (1 point) (b) (6 pts) Outline a sequence of reactions that would be suitable for the preparation of the following compound from the - indicated starting material and any needed reagents. The synthesis will require more than one step. 1-bromo-2—propanol from 2-propanol ’31" U i; 133$. 7.17 {5- 2P“; 5 . Mechanisms (14 pts) (a) Provide a stepwise mechanism, using arrows to show electron movement, to account for the formation of the product in the following reaction. (6 pts) (b) Provide a stepwise mechanism, using arrows to show eiectron movement, to account for the formation of the products in the following reaction. (8 pts) CD OH / u , H???” *r ii w \“SO’H i \ x W. . _ H /\,< J 1% w J ...
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key exam 3 - kt»! ' Ext-“‘03 2 1. (19 pts) (a) Circle...

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