F14 mock exam 3 KEY - l Name{i Fall 2014 CH 2010 MOCK EXAM...

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Unformatted text preview: l. . Name: {i Fall 2014 CH 2010 MOCK EXAM 3 11/18/14 1. Label each chiral carbon in the structures below with the correct (R) or (S) designation. Classify each pair as enantiomers or identical. CHZOH CH3 H30 OH HO“' Br {L Cl g W H H p, H“:- HOIi' H S 3 HO ' Br b. 9‘ Heal me we» > e “\(3\VL'\ lav—eff) \Z/ HO : F HIH .. F ; F C. c. \ HO E7 E2— in), {mAuJJt g“ kg {\Alfitkl S 2. Identify the chiral carbonls) with an asterisk (*) for each compound below. HO' F d. 5 3. (a) How is each compound (a, b, c, and d) related to the simple sugar D—erythrose? is it an enantiomer, diastereomer, or identical? (b) How are a, b, c, and d related to each other? H H ?H HO CHZOH 0 0 OH H OH H O\ ,H H OH \gfvx‘lW t :2,\ g y’xr/‘rn’hcw-é' V; H OH —_"‘ —--*--- CH2OH QHZOH H I D— HO H Erythrose H 0'“ “OH I ‘ H . OH (2R 3R) H CHZOH i ’ O H H’CQO C d LEW-(f1 ALH‘ {Cm‘etj- L C‘- S {gwiffi ' (b) enantidmers: (@\_ andfi); (C_ and cl_) diastereomers: (“it and i ); (EL ands—i ); (‘0 and C ); ( ‘2.) and (‘3 ) 4. Name each of the following (specify R/S as needed}. CH3 H CH2CH3 Br -' Z-‘aroms‘iuhwe Qui\_-L_ hr°M§Mu¥¢yKfi 5. For the following 5N2 reaction (yes, that’s a Fisher projection): ——-. a. Identify the nucleophile, electrophile (substrate), and leaving group. b. Predict the product. Indicate proper stereochemistry. awoke ¢9Lulc L“ .5 + CN' CM H‘ CHtCE-‘i" elcdcmq .l: L. GK 6. For the following in; reaction: I H20 (S)— CHa—CHZ—Cl-ll—CHs + OH‘ —- /\{ ’V /\5/ old— OH a. Predict the products. b. What would happen to the rate of reaction if the concentration of OH" was doubled? Why? M‘ fir“: change, bl; rq’ce talk 9-7:} x-or 3M\ c. What would happen to the are of reaction if the alkyl halide was changed to 1-iodobutane? Why? \fi 0 c hmti Q20 ‘ \‘ke rm“ monk; occur \atat SA\ ‘46.. fill. (aflo‘ c” w: 5r- W M - 7. For each pair identify which compound would react faster under ficonditions? 0' )</ a. A b. Br 8. Classify each of the following solvents as protic or aprotic. i NH 9 CHCl / 3 3 H I? /S\ Qgrdhc groin. mQrdK u. OLQ'd-k\ ‘- 9. Which of the following reacts fastest with methanol by the 5N1 mechanism? CchHchchQCHzBr . (CH3)3CCH28F 1 Br 10. Which is the stronger nucleophile? a. or H2O H20 0r @ 11. Identify the products. ecu. C93 Br CH3CH20H >4; ——r- 0 ll NaBr /\/\O_S_OCH3 _* M ll (3 r O 12. Identify the product and circle the preferred mechanism. KI (CH3)20HBF ———>- acetone 8N1 or (8N2 ) 13. ldentifv the two starting alkyl halides needed to prepare the products shown. u. r 9:? >0. 9 NaCN l : CN X H20 OH DMSO . X 14. For this elimination reaction, assume a stepwise process and draw the mechanism. -————_ 15. Identify the major product in these elimination reactions. Cl NaOCH20H3 16. Identify the major product for each of the following E1 reactions. OH \ ©/J\/ H2804 m />( EtOH /______< 17. Propose a three—step mechanism for the dehydration of the following alcohol. OH H2804 0/ heat 3) -. de—ei lg“ ———» * “1-O- HG / a. T 9"" “M ;f .. ‘3 -a\ 18. Name the structure for (a) and draw the structure for (b). (5) _ 2., 2 "J 0‘“ ‘1‘ Art“ an (a) AO'wH (b) <‘ m h3.%—ea\v-t:k\~‘t[<\l.(—LO fenfiqnd M be 19. From the pairs below, circle the one with the lowest pKa and explain your choice. /\OH or . or \~/\OH Tweed“ eQth as u gamma“; w =*--\<—°~s'*3 $HM£\L%¢-5 CA3 Care-3": 20. Identify the reagents required to accomplish the following transformations. OH Br o0, Inc—1n. O/‘\ P (SF—5 O/\ /LOH ACI ...
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