Summer 2005 Test 2

Summer 2005 Test 2 - ORGAN“; CHEMISTRY TEST 9 NAME fl...

Info iconThis preview shows pages 1–7. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 6
Background image of page 7
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: ORGAN“; CHEMISTRY TEST 9 NAME fl cfi- ~«d Dr. Wells summer i score = opscan * 75/19 + essay = Li * 75/19 +15“ = [Pub in. is h- EssayA 10 points. 19k“ 7 Ckh‘l' on b k { 7c \ Compound X is trans—l—fluoro—2—tert—butylcyclohexane. ((0% L) M Draw the planar conformation of X Write the IUPAC name for X. ch 41:” A Circle one: Compound X is achiral . ‘Hr‘ Ch. ‘ I Q? all of the 4” carbons, El all of the 3“ carbons= A all of the 2° carbons, 0 all of the 10 carbons. Draw the ring-flip equilibrium of the chair conformation of X Discuss which chair conformation is the most stable. Essay B 5 points. Inspect compound Y below. K The best name for compound Y is S 0b "" 3 “I " A\bflm hamlet Circle one: Compound Y is achiral _ Y {5 nssf M960" Essay C 10 points. Write the complete mechanism (Show electron pair movement with curved arrows for each step) for the 8N2 reaction below. — Draw all lone pairs of electrons. - Identify the rate determining slow step and any fast steps. - Identify any intermediates (with [ ]) or transition states (with [ ]1) — Draw the product(s). — Write the rate equation for the substitution. (Le. rate = k ........ ..) reaction CH3 I OH ‘ Clfi—TP—I > H product(s) mechanism 4: Consider compounds 1 - 5 for questions 1 i 6. CH (9 ‘E CH ‘5 H CH3 3 :P 3 5‘ Cl \ {a :/H “1 CH3 ®§ Cl F . ®C”’Hl CIWHW' C\ / ’CH3 C"”H” H'@ F HW“ @ CH3 H F H/©\ / H CH3 F 1 4 [CL] = —140 2 3 1. Compounds 1 and 2 are 2. Compounds 2 and 3 are C. 3. Compounds 3 and 4 are E 4. Compounds 4 and 5 are Q) A. identical and meso B. enantiomers C. diastereomers D. constitutional isomers E. not isomers S. The best name for compound 5 is 6. The specific optical rotation for 5 is A. difluorobutane A. —140 § B. (R/S)—1—fluoro-2—fluorobutane B. 00 j ’i’ 4- mm C. 1,2—di-R-1-fluoro—2—fluorobutane C. +14O "' n“, evfl,‘ D. (2R, 3R)—2—fluoro-3-fluorobutane D. +280 ‘ E. (2R, 3S)—2,3—difluorobutane ® not enough info \‘bowa- Consider enantiomers L and M for questions 8 — 9. [0th = + 70° 7. Eddie mixed 0.37 g ofL with 0.45 g of M. This mixture would be called C- A. racemic B. disteric @ D. dodemeric E. optically pure 8. This mixture would have a specific optical rotation of 0. A. +122 OHS “0.35.9 ' +6.8 Cosh. : fig—r “70° -.; + (oft % C. +5.6 'i 0;”? +0.31, /‘\ D. 0 E. w“10.3 (a)? (NEWka 3 9. Aseparate mixture of L andeith [Ct] =749‘J would containW%L m.) “a? A. 10 o : 5 o B. 15 “laid 51 26 C703 9‘” 5 C 27 c a?” "a" ' ea : 0.70 36 ' f 160 D. 50 C, CE) 85 poere): car. -— C'“"‘°’°L) ............ . ah. i. . .L. . 3; K - fig»? ;i9'.,:L.”L;.L3r" ' 9‘;.;54;é'coo.. {i 10. Consider the planar conformation of cis—1,2—dimethylcyclohexane. Which H’s could be , .— 9 1" replaced with a third methyl group to give a trimethylcyclohexane that is achiral ? T A. all ofthem B. aj 11. Which alkyl halide substrate would you expect to undergo E1 reaction most rapidly ? A. (CH3)3CF B. (CH3)3CC1 .1 ‘bd‘rb‘j )fomp. C- (CH) CB VD CD) (CHiiiclr (at? C h E5k53§ni¢3 E. they would all react at the same rate 12. Which of the following statements is true of 8N2 reactions of alkyl halides in general ? A. The rate of an SN2 reaction depends on the concentration of the alkyl halide/ B. The rate of an SN2 reaction depends on the concentration of the nucleophile.\/ C. The rate of an 8N2 reaction depends on the solvent.1/ E D. Only two of the statements are true. R "Vlad- “l h“? t‘ ® A, B and C are all true. 1 3r Ace) mii (Av, h CJa-‘JCM AWN ‘“ "“ rick Wm'iifdv‘ ' Consider the ring flip equilibrium of compound 13 and 14 below for questions 13 — 16. iPr Me H AG“ = 4 kJ/mol H ~_.—. Me iPr H 13b 13a H Me Et H H H 14a H 14b Me = methyl, Et : ethyl, iPr = isopropyl 13. The most stable conformation of compound 13 is . A B. 13b C. neither, they are degenerate D. not enough information 9’ \Mn.) [5447,1/ fiflw‘P’ “9/! Lupmgizmfl 14. If compound 13 is at equilibrium at room temperature we would expect to find 7% of the molecules as comformation 132:. A. 99.9 C. 50 D. 17 E. 0.1 15. The free—energy difference between 143 and 14b would be kJ/mol. A. greater than 4 @1555 than4 +|~L AJH‘S/ent ‘90 Hero“ D. 0 , g 13. not enough info me fi l5 l¢§5 yr,“ Jr“: Ax“ H’qu Bai’“"" 16. Compound 14 is . ' r- A. a chiral compound @an aehiral compound N ’fi L l5 Consider the reaction of butylbromide with F" ion in dimethylsulfoxide for questions 17-18 CH3CHQCH2CH2BI‘ + F7 ------ --> CH3CH2CH2CH2F ‘5‘ Br— 17. What effect on the rate would result from simultaneously tripling the concentrations of both butyl bromide and F‘ ion ‘? A. no effect B. rate would double 9 C. rate would triple \d . rate would increase by a factor of 6 (g rate would increase by a factor of 9 5 [6.4 “.3 7r; 3)- ‘Jm’nL afflhL 18. What effect on the rate would result from switching from ethanol to DMSO as solvent ? A. no effect 0 B. rate would decrease 1 © rate would increase /5\ CH3_ CH2" OH D 1111 ossible to redict' must be determinedb ex ' ~ t H3C CH3 C/ v 13 ~ p = y Perlmcn DMSO ethanol 19. is considered to be the founder of the field of stereochemistry because he discovered enantiornerism by separating the enantiomers of tartaric acid. A. Alexander Fleming b B. Francisco Cannizaro C. Linus Pauling ® Louis Pasteur E. Justis Liebig ...
View Full Document

This note was uploaded on 06/19/2008 for the course CHEM 227 taught by Professor Wells during the Summer '07 term at Campbell.

Page1 / 7

Summer 2005 Test 2 - ORGAN“; CHEMISTRY TEST 9 NAME fl...

This preview shows document pages 1 - 7. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online