Summ08Ex3

Summ08Ex3 - "Grade or Education" = CHEM 2261/01...

Info iconThis preview shows pages 1–9. 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

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

View Full DocumentRight Arrow Icon
Background image of page 8
Background image of page 9
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: "Grade or Education" = CHEM 2261/01 Summer 08 Exam 3 Chapters 7-9 Find the substitution product(s) of the reaction of (25,3R)—2—chloro—3—methylpentane + high concentration of CH30' from among the numbered structures shown below. Choose the CORRECT statement from the multiple choices. __ A. 1_ is the sole product of this reaction. __ B. 1 is the sole product of this reaction. __ C. 1 is the sole product of this reaction. __ D. __ E. i is the sole product of this reaction. Rationale: Chapter 8 Problem 52b 1 and i are both products of this reaction. 2- What two compounds could be used to produce the compound whose structure is shown below from a Diels—Alder reaction? g ,COZCHS Pick the structures of the two compounds which can be used in this Diels—Alder reaction from the numbered choices below. COZCH3 (302cm3 C Cr C U :> CH2 1 2 § fl § § Compounds i and Q can be used in this reaction. Compounds 1_ and ; can be used in this reaction. A B C. Compounds 1 and Q can be used in this reaction. D Compounds ; and i can be used in this reaction. E Compounds ; and i can be used in this reaction. Rationale: Chapter 7 Problem 64b 3. Find the elimination product(s) of (ZS,3R)—2—chloro—3—methylpentane + high concentration of CH30' among the numbered structures below. Choose the CORRECT product of this reaction. CH3 CH3 CH CH CH CH-2CH CH3 CH3 : _ : ,\2 : 3 : 3— : 3 H CH-ZCH3 H CH.2(3H3 H CH3 H CH:CH2 g l—L IN l-h 1_ and i are both products of this reaction. 1 is the product of this reaction. 1 is the product of this reaction. is the product of this reaction. 1_ i is the product of this reaction. Rationale: Chapter 9 Problem 48b Rank the compounds whose structures are shown below in order of INCREASING acid strength (weakest acid listed first). QOH QCHZOH QCOOH 1 2 Q __A. 1_<i<; __ B. 1_<;<i __C. ;<;<1_ __ D. i<1_<; __ E. ;<1_<i Rationale: Chapter 7 Problem 18 Choose the CORRECT substitution product of the reaction of 3—bromo—2—methylpentane + CH30H from the numbered structures shown below. 9H3 9H3 9H3 CH'3Cl3—CH'2CH'2C H3 CH'3CH' CI3H'CH'2C H3 CH'SCE— CH'ZCH'ZC H3 OCH3 OCH3 OH 1 2 § (EH3 9H3 CH'SCH'CIDH'CHéCH3 CH'SCH'CH'ZQH'CH3 0H OCH 4 § 3 i is the product of this reaction. 5 is the product of this reaction. 1 is the product of this reaction. is the product of this reaction. 1_ a is the product of this reaction. Rationale: Chapter 8 Problem 45e For the target compound whose structure is shown below choose the multistep synthesis which could be used to prepare it from the given starting material. 9 CH:CH2 CH-ZC-H —> A First: Brz/CHZCIZ; Next: excess 'NHZ; Finally: HZSO4/HgSO4 B. First: Brz/CHZCIZ; Next: excess 'NHZ; Finally: 1. disiamylborane and 2. HO', H202, H20 __ C. First: HBr/CHZCIZ; Next: 'NHZ; Finally: 1. BH3/THF and 2. HO', H202, H20 D First: Brz/CHZCIZ; Next: excess 'NHZ; Finally: HZSO4/HZO E First: Brz/HZO; Next: 'NHZ Rationale: Chapter 9 Problem 31 b Find the kinetic and thermodynamic products of the reaction of one equivalent of HCI with 2,3—dimethyl—1,3—pentadiene among the numbered structures below. Choose the CORRECT statement from the multiple choices. CIDH3 CIDI CH3 CH3 CIDH3 I CH'ZCZC— CH-ZCH3 CHé)C-C:CH'CH3 CHéCZC— CH'CH3 CH'ZCH'CZCH'CH3 l | l | l l l Cl CH3 CH3 CH3 Cl Cl CH3 1 2 § 5 __ A. i is the kinetic product and 1_ is the thermodynamic product. __ B. 1_ is the kinetic product and i is the thermodynamic product. __ C. i is the kinetic product and 1_ is the thermodynamic product. __ D. g is the kinetic product and i is the thermodynamic product. __ E. i is the kinetic product and g is the thermodynamic product. Rationale: Chapter 7 Problem 68a 8- Rank the ions whose structures are shown below in order of DECREASING nucleophilicity in methanol (strongest nucleophile listed first). 0 || _ _ . CHéC-O CH-sCH-ZS CHéCH-ZO 1 g g __A. 1>i>1_ __B. 1_>i>; __C. l_>;>; __D. i>1>1_ __E. ;>1_>i Rationale: Chaptr 8 Problem 42a 9. Shown below is a curved—arrow mechanism for converting structure 1_ into structure Q. Which structure has the curved arrow(s) associated with it drawn INCORRECTLY ? cH3 cH3 H20. CH3 <>~CH§Br _. H —> —> + 3 1 2 + Br' _ T + 0|:\'I OH H 0: CH3 2 CH3 + —> + H30 4 5 __ A. 1 __ B. i __ C. i __ D. 1_ __ E. ; Rationale: Chapter 8 Problem 62a 10- Two curved—arrow mechanisms are shown for the reaction of 4—bromocyclohexanol with HO' to form substitution products. Figure out the substitution mechanism(s) for the reaction of cis—4—bromocyclohexanol and trans—4—bromocyclohexanol with HO' to form product(s). Choose the CORRECT statement from the multitple choices. .. :OH O HaeQBr er #9 mechanism 1 HO Br " HOOOH \J mechanism 2 cis—4—bromocyclohexanol undergoes mechanism ;. Neither cis—4—bromocyclohexanol nor trans—4—bromocyclohexanol undergo mechanism ;. A B __ C. cis—4—bromocyclohexanol undergoes mechanism 1_. D trans—4—bromocyclohexanol cannot react by either mechanism. E __ . Both cis—4—bromocyclohexanol and trans—4—bromocyclohexanol undergo mechanism 1_. Rationale: Chapter 9 Problem 55a 1 l . Use the numbered structures shown below to choose the CORRECT statement from the multiple choices. /\/\CI *0 3 %~CI CI § § __ A. (CH3)3CBr will react faster with CH3CHZOH than it will with H20. __ B. (CH3) ZCHS' will react faster with 1_ than CH3S' will. __ C. i will not react with HO'. __ D. i will react with H20 faster than i will. __ E. ; will react with HO' faster than 1 will. Rationale: Chapter 8 Problem 48 12. 13. Which of the structures shown below has delocalized electrons? CH2=CH-CH-2CH=CH2 CHgCHg-V-H-CH-ZCHZCHZ Z/ ..\> N H g (i " 9. 1 2 fl 5 structure 1 structure ; A B C. structure; D structure; E structure 1_ Rationale: Chapter 7 Problem 3 Name the dienes shown below and rank them in order of INCREASING stability (name of least stable diene listed first). ‘3”3 9H3 CH'3CHICH'CHZCH-CH3 CHZZCH-CHECHZCH2 CH'3C=CH-CH=C-CH3 ()H-3(3H:()H-CH:CH2 __ A 1,5—pentanediene < 2,5—pentanediene < 2,5—hexanediene < 2,5—dimethyl—2,5—hexanediene __ B 1,4—pentadiene < 1,3—pentadiene < 2,4—hexadiene < 2,5—dimethyl—2,4—hexadiene __ C. 1,3—pentadiene < 2,4—hexadiene < 1,4-pentadiene < 2,5—dimethyl—2,4—hexadiene __ D 2,5—dimethyl—2,4—hexadiene < 2,4—hexadiene < 1,3—pentadiene < 1,4—pentadiene __ E 2,5—dimethyl—2,5—hexanediene < 2,5—hexanediene < 2,5—pentanediene < 1,5—pentanediene Rationale: Chapter 7 Problem 10 14. 15. Figure out what the major elimination product(s) obtained from E2 reactions of hydroxide ion and the alkyl halides with structures 1_ and 2 are. Choose the statement which is CORRECT from the multiple choices. (3H3 (3H3 (3H3 9H3 CH-SCH-(IEH-CH-ZCHS CHéCH-(IDH-CH-ZCHS CHéCZCH-CH-ZCHS CHéCH-CHICH-CHs CI F 1 2 § 5 A. 1_ reacts with hydroxide to give 2 as the major E2 product and 2 reacts with hydroxide to give 1 as the major E2 product. B. Both 1_ and 2 react with hydroxide to give 2 as the major E2 product. Both 1_ and 2 react with hydroxide to give 1 as the major E2 product. D. 1_ reacts with hydroxide to give 1 as the major E2 product and 2 reacts with hydroxide to give 2 as the major E2 product. E. 1_ and 2 react with hydroxide to give E2 products which are not shown in the structures above. Rationale: Chapter 9 Problem 4(b,f) By looking at the numbered structures below find the ma'or elimination product(s) of a mixture of the two stereoisomers of trans—1 —chloro—2—methylcyclohexane for the conditions specified in each of the multiple choices. Choose the CORRECT statement. H30 NW3 M “30% 1 2 § __ A trans—1—ch|oro—2—methylcyclohexane + high concentration of CH30' yields 2. __ B trans—1—ch|oro—2—methylcyclohexane + high concentration of CH30' yields 1_and 2. __ C. trans—1—ch|oro—2—methylcyclohexane + CH30H yields 2 and 2. __ D trans—1—ch|oro—2—methylcyclohexane + high concentration of CH30' yields 1_and 2. __ E trans—1—ch|oro—2—methylcyclohexane + CH30H yields 1_ and 2. Rationale: Chapter 9 Problem 38(c,d) 10. 11. 12. 13. 14. 15. Answer Key "Grade or Education" CHEM 2261/01 Summer 08 Exam 3 Chapters 7-9 1 ...
View Full Document

This note was uploaded on 12/30/2011 for the course CHEM 2261 taught by Professor Crowe during the Fall '08 term at LSU.

Page1 / 9

Summ08Ex3 - "Grade or Education" = CHEM 2261/01...

This preview shows document pages 1 - 9. Sign up to view the full document.

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