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Answer_Key_Exam_II

Answer_Key_Exam_II - Midterm Examination II CHM 231 Fall...

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Unformatted text preview: Midterm Examination II CHM 231 Fall, 2004 Dr. Gust Time limit: 50 minutes NAME: ‘4 J W C Answer on these sheets Total points = 100 SIGNATURE: W In the questions below, circle the letter corresponding to the correct answer, or fill in the blank. They are worth 3 points each. There is only one correct answer to each question. If more than one is circled, your grade for that question will be zero. 1. Which compounds contain stereocenters? I) l-chloropentane II) 2-chloropentane III) 3-chloropentane IV) 1,2-dichloropentane a) I, II b) III, IV 0 I, III II, IV 2. How many stereoisomers are possible for the following structure? Sm ‘3 CHgCHfiIHCOH NH; a) l b) 2 c 3 fl) 4 3. What is the relationship between these two structures? Br c1 ' Br H 3.) identical structures (homomers) b cnantiomers diastcreomers . constitutional isomers 4. The following structure contains 5 stcrcocenters. 3% N 0.0 0 OH 5. Which are the approximate carbon-carbon bond angles at positions I and II in the following compound? I CH3 II a) 109°, 109° b 120°, 180° 120°, 109° (1) 109°, 120° 6. Which of the following alkcncs do not show cis-trans isomerism? I) 2-mcthyl-2-hexene II) 1-ohloro-1-butcne III) 1-methylcyclohcxene IV) 2-mcthyI-3-hexenc a) I, II b) III, IV c 11, III, IV I, III 7. 9. Which alkenes have E configurations? (I? t? - Ho—q fC—OH 01‘ {CHZCI IC=C\ IC=C \ . H H H CH3 I II a) I, II 1) II, III III, N (1) II, IV The number of isoprene units in menthol (shown below) is CH Clil H2C F \ f C: C " \ H3C C1 III Br Cl \ ; C=C / \ H3C I IV 9- . Which point on the potential energy diagram below represents the intermediate? _6 reaction coordinate 10. Using Markovnikov’s rule, predict the position of the Cl atom in the major product from the reaction of 1-methylcyclohexene with HCl. (Sec. 5.3) L Ann—b- /C B) ED 11. Arrange these carbocations in order of increasing stability (least to most). 69 A‘g <:>— H3C® #6) I II III IV a I, II, III, IV @111, I, 11, IV 0) 11, IV, I, III d) I, III, IV, 11 12. Which is the major product from the reaction of propene with 0504/ROOH? a) 1-propanol b 2-propanol ,2-propanedicl d) 1,3-propandiol 13. Which is the major product from the reaction of cyclopentcne with Brz? BL’HH Br HAH Br | i H I i Br b) c) d) 14. Which statements apply to an SNI reaction? I) The rate limiting step of the reaction involves the alkyl halide and the nucleophile. II) The order of reactivity is methyl > 1°>2°>3°. III) The rate limiting step of the reaction involves only the alkyl halide. IV) There is an intermediate carbocation. a LII III, IV 0) LIV cl) III 15. Which statements apply to an 8142 reaction? I) The rate limiting step of the reaction involves the alkyl halide and the nucleophile. II) The order of reactivity is methyl > l°>2°>3°. III) The rate limiting step of the reaction involves only the alkyl halide. IV) There is an intermediate carbocation. ' .I,II b) III, w c) I, IV d) II, Iv 16. Which alkyl halide leads to the product shown, in an E2 reaction? CH2 Product C1 CH2CI 5» mic: @fij $01.; 17. Which statements are true for an El reaction? I) The rate limiting step of the reaction involves only the alkyl halide. II) The rate limiting step of the reaction involves the alkyl halide and the base. III) There is an intermediate carbocation. IV) The order of reactivity is 1°>2°>3°. .1, 111 b) 11 c) I, III, 1v (1) II, IV 18. Which are secondary alcohols? CH3 CH3 H30 H H OH | \ x Q Hes-0H ,czq OH CH3 H (IZHCHg OH I II III IV a) I, III b 11, III III, IV (1) I, IV 19. Arrange the following in order of increasing ability to hydrogen bond (lowest first). 1. CH3—- H II. CH38—H III. CH30-H IV. HOwH 20. Which reagents do not cause the following conversion? HO—C>-CH3 -———"—- Cl~<:>—CH3 HCl (:12 soc12 NaCl -——-—-—’ —’ _..__b h‘ I II III. IV a) I, II b) II, III @11, IV d) I, 111 21. Which is the best method for making the following conversion? OH | CchHZCHzOI-I ”my. (£3,0ch3 H PO ' 3 3 dilute b) P” H2 d11ute heat H2304 H2804 HPO @450” 0) FCC d) 3 4 ———’. 22. Which is the product of the following reaction? <:>—CH20HO «BE» 0 308 [email protected] c) H3CCCHZCH2CH2CH 23. Which is the major product of the following reaction? _ CH3 CH3(IJHCH20H £04,, M2,. heat ‘EH3 3% a) CHaCHfiH b) CHgCHfiOH 0 0 CH3 | @CHgCHCHg d) CH30HZCH20H3 24. Arrange the compounds below in order of increasing acidity (least first). OH OH OH 0? fCHa I II III IV a) I, II, III, IV b 111, I, 11, IV IV, 11, I, 111 d) IV, II, III, 1 25. Arrange the compounds below in order of increasing reactivity toward electrophilie aromatic substitution (lowest first). CH3 Cl OH 0% I II III IV a III, II, I, IV IV, II, I, III C) III, LII, IV d) I, II, III, IV 26. Which is the major product of the following reaction? 0CH3 0 N02 I l H3€CC1 mm—b- AlCl3 OCH3N OCH3N 0CH3 0CH2CCH3 a) 0 W601» «ctr H3C(\j‘ 0CCH3 0 O¢CCH3 2'7. Which is the major product of the following reaction? ‘3' ll CCH2CH20C1 A1013 I I -—-———-—-I- O a) b) was; 28. Which is the major product of the following reaction? HNOg (312 H2504 Fe013 1 -chloro-3 -nitrobenzenc c) l-chloro-Z-nitrobenzene d) a mixture of 1-chloro-4-nitrobenzene and 1-chloro-2—nitrobenzene & 1-chloro-4-nitrobcnzcnc For the questions below, circle the correct answer, true (T) or false (F). Each question is worth 1 point. 29. ('3 F The following structures are enantiomers. H CI Cl“‘7l\ H“7l\ H0 CH3 HO CH3 30. @ F The following structures are diastereomers. 31. T ® The following structures represent isomers. \" : : x“ ‘| 32. T @ The reaction represented by the reaction energy diagram below is endothermic. M\ reactlcn coordlnate 33. (9 F The activation energies of the reaction represented by the above reaction energy diagram (question 32) are noted as A and B. 34. ('19 F The major product of the reaction of catalytic hydrogenation of 1,2- dimethylcyclohexene is cis-l,2-dimethylcyclohexane. 10 35. T63 36. T® 37. 6) F 38. T® ,0 H3C 39. [email protected] / \ CH3CHZCHZCH2 H > CH3CI-IZCH2/ 40. [email protected] 41. T® 42. @F 43. @F \H > CH3CH.{ The following alkyl halides are listed in order of decreasing SNI reactivity. +0 > Hac—Cl > >'CI > /\01 The following alkyl halides are listed in order of decreasing 3N2 reactivity. /\Br > /\| > /\F 3- /\CI The product of the reaction of methanol with sodium metal is sodium methoxide. The following compounds are listed in decreasing boiling point order (highest first). 0 o 0 “‘H > cnjcnzcnz/ “H > CH30H20H20H5/ “H The following compounds are listed in decreasing order of solubility in water (highest first). 0 O 0x. 0\ “‘H > CH30H{ H > me” _H The product of the reaction of toluene with concentrated nitric and sulfuric acid is m-nitrotoluene. The product of the reaction of isopropylbenzene with chromic acid is methylphenyl ketone. The product of the reaction of benzoic acid and chlorine/A1013 is m-ehlorob‘enzoic acid. The following compounds are listed in decreasing order of reactivity toward electrophilic aromatic substitution. seas The following compounds are listed in decreasing order of reactivity toward electrophilic aromatic substitution. $6035 11 ...
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