Summ09Ex4

Summ09Ex4 - "Grade or Education" = 1 CHEM 2261/01...

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Unformatted text preview: "Grade or Education" = 1 CHEM 2261/01 Summer 09 Exam 4 Chapters 10, 11, 14 1 . Pick the choice which CORRECTLY describes how the following synthesis could be carried out. Note the abbreviations used in the multiple choices for several reagents or solvents whose structures are shown below the synthesis. 9 CH3 CH —> 'i + _ /O\ i? (5“: - N\ 0' CH3 E0 RCO3H tert-BuO' Et20 PCC A First: BrZ/hv; Next: HO‘; Finally: HZCrO4 B First: BrZ/hv; Next: HO‘; Finally: Pcc __ C. First: BrZ/hv; Next: tert-BuO' ; Next: E0; Finally: HO— D First: BrZ/hv; Next: Mg/Etzo; Next: H20; Finally: HZCrO4 __ E. First: BrZ/hv; Next: Mg/Etzo; Next: H20; Finally: Pcc Rationale: Chapter 11 Problem 19b 2- Figure out the names of the five compounds whose structures are shown below. Choose the one which is CORRECTLY named in the multiple choices. OH OCH3 CHICH2 CH3 (3 (j (j (j a c e f 9 Compound e is styrene. Compound a is phenol. A B C. Compound 9 is anisole. D Compound c is phenylnitrile. E Compound f is toluene. Rationale: Chapter 14 Problem 35(a,c,e,f,g) 3. Pick the choice which CORRECTLY describes how bromocyclohexane can be converted into the compound whose structure, labelled 51 c , is shown below Note that abbreviations have been used for some reagents used in the proposed syntheses; structures of these reagents are also shown below.. OH O /o\ Icl) H3C _ H HZC—CHZ R-C- OOH “309—0 H30@fi—CI " H30 0 51c E0 RCO3H tert-BuO' TsCl A. First react the bromocyclohexane with TsCl . Next react with E0 . Next react with tert -BuO-. Finally react with ncosfl. —— B- First react the bromocyclohexane with tert - BuO' . Next react with E0. Finally react with: 1. CH3MgBr, followed by 2. H+. —— C- First react the bromocyclohexane with tert - Bud‘ . Next react with ncoafl . Finally react with: 1. CHgMgBr, followed by 2. H+. —— D- First react the bromocyclohexane with _OH. Next react with TsCl. Finally react with CH3MgBr. E. First react the bromocyclohexane with Mg/ether. Next react with E0. Finally react with CHgBr followed by H+. Rationale: not in current text 4- Find the major product of the reaction shown below. Ignore stereochemistry. (EH3 h CH-SCH-ZCH-CH-ZCH-ZCH3 + Br2 —.V ? 9H3 ‘3“3 9H3 Br-CHECH-ZCH-CH-ZCH-ZCHS CH'BQH'CH'CH'ZCH'ZCH3 CH-aCH-ZCH-(IDH-CH-ZCH3 1 Br 2 3 Br (IDH3 9H3 CH-SCH-chs-CH-ZCH-ZCH3 CH§H20H'CH2$H'CH3 Br 4 5 Br __ A. 1 is the major product of this reaction. 4 is the major product of this reaction. B __ C. 3 is the major product of this reaction. D 2 is the major product of this reaction. E __ . 5 is the major products of this reaction. Rationale: similar to Chapter 1 1 Problem 22c 5- By looking at the labelled structures below figure out which of the multiple choices specifies the CORRECT product of a reaction. 0 O (I)H ll SCH-20Hon OCH-CH3 O/CH-ZC-OH f d i 1 e HO-CH2 OCH3 CH30'0H2 OH 2 3 4 A ef + H+/CH30H a d B ef + H+/CH30H a 4 —— C- ef + CH30_/CH30H a 4 D d + HZCrO4 —> 2 E i + HZCrO4 —> 1 Rationale: similar to Chapter 10 Problem 38 6- Choose number of the CORRECT structure of the product of the following reaction: CH-CH 2 3 Nazcr207, H+ I? A . CH3 ; ,CH-ZCOOH CHZCH3 CH-ZCOOH COOH ; COOH COOH COOH CH3 Cl H3 COOH 1 2 3 4 5 WPCW? d-hNUIu Rationale: moved to Chapter 16 Examine the reaction mechanism shown below for the conversion of REAC46a into PROD46a. Based on this mechanism what is the CORRECT structure of PROD46b? II + :o OH :OH :'oH l CH3 (ll CH3 + CH CH + CH31> JCH3__ 3 3 H CH 3 REAC46a CH3\=B PROD46a H+ —> PROD46b H30 CH3 REAC46b :23 :'oH :BH :ICIDH :'(')H CH3 CH3 CH3 CH3 CH CH CH CH 3 3 3 H3C 3 CH3 1 2 3 4 5 __A. 2 __B. 4 __c. 1 __D. 3 __E. 5 Rationale: Chapter 14 Problem 51b Classify each of the five numbered structures below as aromatic, nonaromatic, or antiaromatic. (Hint: If possible a ring will be nonplanar to avoid being antiaromatic.) Choose the CORRECT statement. + CH2 \ I Q v / 7 + .. 1 2 3 4 5 A. 1 is nonaromatic. __ B. 3 and 5 are antiaromatic. __ C. 1, 3, and 5 are aromatic. __ D. 2, 4, and 6 are aromatic. __ E. 5 is antiaromatic. Rationale: Chapter 14 Problem 36 Find the major products of the reaction of 1—methylcyclohexene with the reagents specified in the multiple choices. Choose the response which CORRECTLY matches one or more structures below with a particular reaction. Ignore stereochemistry. CH3 HSC Br CH3 H30 Br H3O Br Br Product 1 Product 2 Product 3 Product 4 Product 5 A. Products 1 and 2 are major products of the reaction of 1—methylcyclohexene with B r2/CH2CI2. B. Product 3 is the major product of the reaction of 1—methylcyclohexene with HBr. Products 3 and 4 are major products of the reaction of 1—methylcyclohexene with B rZ/CHZCIZ. D. Product 4 is the major product of the reaction of 1—methylcyclohexene with NBS/A/peroxide. E. Product 3 is the major product of the reaction of 1—methylcyclohexene with HBr/peroxide. Rationale: Chapter 1 1 Problem 18 10. Examine the proposed 6—step mechanism shown below for the conversion of alcohol 1 4cR into bromide 1 4cP in the presence of HBr. Which of the steps shown below is/are WRONG for this reaction? ll CH3 VH CH3 14cR CH3 CH3CH3 CH3 + + H-OH ste_p3’ step4 $043 step5 CH3 3 _’ —’ CH3 CH3 it + :Br:_ fl. Br CH3 “GP CH3 Step 1 is wrong. Step 2 is wrong. A B C. Steps 1, 2, and 3 are wrong. D Step 6 is wrong. E Steps 4 and 5 are wrong. Rationale: Chapter 10 Problem 12c l 1- Part of the mechanism is shown for the reaction in the figure below. Which of the choices BEST describes what happens in the very next step of the mechanism (not shown)? CCI 3 peroxide + HCCI3 —> 00 RO—OR —> 2R0- H W ' + I ’ ‘ ’ __ A. The 8—membered ring radical abstracts a hydrogen atom from an HCCI3 molecule. __ B. The 8—membered ring radical abstracts a hydrogen atom from an ROH molecule. __ C. The lone electron (radical) in the position represented by the rightmost resonance structure attacks the more remote double bond on the exact opposite side of the 8—membered ring forming a structure with two connected 5—membered rings. __ D. A 1 ,2 shift of a hydrogen atom occurs, moving the free radical electron one position further counterclockwise along the 8—membered ring. __ E. The radical on the 8—membered ring attacks a peroxide molecule attaching an OR group to the ring. Rationale: Chapter 1 1 Problem 41 12- Choose the synthetic sequence which gives a CORRECT method for preparing 2—phenyl—1—ethanol from benzene. CH'ZCHZOH 2-phenyI-1-ethanol __ A. First: CH3CH2C| and AICI3; next: NBS/A and peroxide; next: tert—BuO_; finally: H20 and H2504. __ B. First: CH3CH2COC| and AICI3; next: NBS/A and peroxide; next: tert—BuO_; finally: 1. BH3 followed by 2. HO‘, H202, H20. __ C. First: CH3CH2C| and AICI3; next: NBS/A and peroxide; next: tert—BuO_; next: HBr/CHZCIZ; finally: HO_. __ D. First: CH3CH2COCl and AICI3; next: Zn(Hg) and HCl/A; next: tert—BuO‘; finally: 1. BH3 followed by 2. HO_, H202, H20. __ E. First: CH3CH2C| and AICI3; next: NBS/A and peroxide; next: tert—BuO_; finally: 1. BH3 followed by 2. HO‘, H202, H20. Rationale: moved to Chapter 16 1 3. Find the product(s) of the reaction shown below and select the answer which indicates the CORRECT product(s). CH3 hv CHZCI CH3 CH3 CH3 Cl 6 Cl Cl 1 2 3 4 The compound labelled 2 is the only correct product. The compound labelled 3 is the only correct product. A B C. All four products are formed by this reaction.. D The compound labelled 4 is the only correct product. E The compound labelled 1 is the only correct product. Rationale: Chapter 11 Problem 22f 1O 14. Using the starting material with the structure shown in the figure below, any necessary inorganic reagents, and any carbon—containing compounds with no more than two carbon atoms, figure out how to synthesize the product having the structure shown in the figure. Pick the choice which CORRECTLY describes how this synthesis might be accompliched. CI CH-ZCH-ZCEN A. First treat the starting compound with Mg and EtZO. Next treat the resulting compound with TsCl. Next react with: 1. ethylene oxide, followed by 2. H+. Finally react with _CEN. B. First treat the starting compound with Mg and EtZO. Next treat the resulting compound with: 1 . ethylene oxide, followed by 2. H+. Next react with TsCl. Finally react with _CEN. First treat the starting compound with CH2=CH2CEN and (Ph3P)4Pd/Et3N. Then treat the resulting compound with excess HZ/Pd/C. D. First treat the starting compound with tert—butoxide. Next react with HZO/HZSO4. Next react with TsCl. Next react with NaCECH. Finally react with HCN. —— E- First treat the starting compound with _OH. Next react with TsCl. Next react with: 1 . ethylene oxide, followed by 2. H+. Finally react with _CEN. Rationale: similar to Chapter 1 1 Problem 25d 11 l 5- Choose the CORRECT structure of the major product of the reaction shown below. CHgH-CH-ZCH-ZOH 1. p-toluenesulfonyl chloride —> ? CH3 _ 2- Q0 CHQQH'CHZCH'OQ CHQCH-CHECHEOQ CH-3c|:H-CH:CH2 | CH 3 CH3 CH3 1 2 3 (IJH3 (IJH3 CHECHECID—OQ CHECH-(f—OQ CH3 CH3 4 5 __ A. 1 is the major product of this reaction. 5 is the major product of this reaction. B __ C. 4 is the major product of this reaction. D 3 is the major product of this reaction. E __ . 2 is the major product of this reaction. Rationale: Chapter 10 Problem 33c 10. 11. 12. 13. 14. 15. Answer Key "Grade or Education" CHEM 2261/01 Summer 09 Exam 4 Chapters 10, 11, 14 1 13 ...
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This note was uploaded on 12/30/2011 for the course CHEM 2261 taught by Professor Crowe during the Fall '08 term at LSU.

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Summ09Ex4 - "Grade or Education" = 1 CHEM 2261/01...

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