Summ10Ex4

Summ10Ex4 - "Grade or Education" =1 CHEM...

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Unformatted text preview: "Grade or Education" =1 CHEM 2261/01 Summer 10 Exam 4 Chapters 10, 11, 14 How many alkyl halides can be obtained from the monochlorination of the alkane shown below? Neglect stereoisomers. (EH3 (EH3 CHSCID-C H-2CHCH3 CH3 Rationale: similar to Chapter 1 1 Problem 4i 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. CH3(|3H-CH-pH CH-ScH-CH-ZCHZCH-ZOH CH3 CH3 0 l? l? l? /\ _ _ _ _ _ H2C_CH2 H30@fi CI R c OOH H3C 0 CI CH3CH20CH2CH3 o A First: TsCl/pyridine; Next: E0; Finally: HO_/HZO B First: TsCl/pyridine; Next: CH2=CHMgBr; Next: RCO3H; Finally: H+/HZO __ C. First: HBr/A; Next: Mg/Et20; Finally: 1. E0 , and 2. H+ D First: HBr; Next: Mg/Et20 ; Next: AcCl; Finally: HZ/Pd __ E. First: TsCl/pyridine; Next: HOCHZCHZMgBr Rationale: Chapter 1 1 Problem 25b 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. OH —> OH 0 9 9H3 2 2 CH3 E0 RCO3H tert-BuO' Et20 A First: BrZ/hv; Next: tert-BuO '; Next: Bra/CHZCIZ; Next NaNHZ (excess); Finally: H+/HZO B First: BrZ/hv; Next: tert-BuO ' ; Next: R603H; Finally: HO- C. First: BrZ/hv; Next: Mg/Et20; Next: E0; Finally: H+/HZO D First: BrZ/hv; Next: HO'; Next: HZCrO4; Next: R603H; Finally: HO- —— E- First: BrZ/hv; Next: tert-BuO ' ; Next: E0; Finally: HO- Rationale: Chapter 12 Problem 19d Figure out which alcohol in each of the pairs shown below will undergo dehydration more rapidly when heated with H2804. Pairs of alcohols share the same letter, ie, a1 and a2 . Choose the CORRECT statement from the multiple choices. CHZOH CH-ZCHZOH OH OH a1 a2 OH CH b1 b2 | OH I c2 d1 : : d2 a1 will undergo dehydration more rapidly than a2 when heated with H2504. c1 c2 will undergo dehydration more rapidly than c1 when heated with H2804. A B C. None of the other choices is correct.. D d2 will undergo dehydration more rapidly than d1 when heated with H2504. E b1 will undergo dehydration more rapidly than b2 when heated with H2504. Rationale: similar to Chapter 10 Problem 34(a—d) 5. 6. 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 H30 Br CH3 H30 Br H30 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 4 is the major product of the reaction of 1—methylcyclohexene with NBS/A/peroxide. __ C. Products 3 and 4 are major products of the reaction of 1—methylcyclohexene with B r2/CH2CI2. D. Product 3 is the major product of the reaction of 1—methylcyclohexene with HBr/peroxide. E. Product 3 is the major product of the reaction of 1—methylcyclohexene with HBr. Rationale: Chapter 1 1 Problem 18 By looking at the numbered structures below figure out which of the multiple choices specifies the CORRECT product of a reaction. [CH CH-sCH-ZCl-I-lq 0 CH3 CH3 | CHéCIEH-CH-ZCH-ZOH CH-sCH-ZCH—CIEHs CH OH OCH3 9H3 CH-3CH-2cl:H-CI>CH3 CHéo OH 3 3 1 2 3 4 A 1 + CH3O'/CH3OH —> 2 B. 1 + H+/CH30H—> 2 c. 1 + H+/CH3OH —> 4 D 1 + CH3O'/CH3OH —> 4 —— E- 1 + CH3O'/CH30H —> 3 Rationale: Chapter 10 Problem 33(d,e) 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 (3'4ch2 CH3 (3 (j (j (j a c e f 9 Compound f is toluene. Compound 9 is anisole. A B __ C. Compound a is phenol. D Compound e is styrene. E __ . Compoundc is phenylnitrile. Rationale: Chapter 15 Problem 35(a,c,e,f,g) 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 \ | Q v N/ 7 + 1 2 3 4 5 __ A. 3 and 5 are antiaromatic. 5 is antiaromatic. __ B. __ C. 1 , 3 , and 5 are aromatic. __ D. 1 is nonaromatic. __ E. 2 , 4 , and 6 are aromatic. Rationale: similar to Chapter 15 Problem 36 9- Work out the curved—arrow mechanism for the rearrangement reaction shown below. OH O H so W 2 4 H20 HO Which of the numbered curved—arrow mechanistic processes shown below is NOT part of your mechanism? OH W m // HO 1 H Cl 2 OH + . HQH HO 3 fif—\k O +///’—\\\\ W HO 4 5 | | W P O W P “Mal-lb Rationale: Chapter 10 Problem 59a 10. Work out the curved—arrow mechanism for the rearrangement reaction shown below. CH3 | : ,CH-ZCH-ZCH-CHICHZ H+ H30 CHECHS Which of the numbered curved—arrow mechanistic processes shown below is NOT part of your mechanism? (|3H3+ CH- H-C— H-CH 20 1} 3 CH 3 A4- | CH-ZCH-ZCH-CH:CH2 H 1 + CH3 2 CH'2CH3 H 9H3 3 B) 9H3 CH-ZCH—gr-CH-ZCH3 CH-2(:|-l2(3H/CI-|:CH2 4 5 WPOW? 01wth Rationale: similar to Chapter 15 Problem 47a Which of the choices lists the reactions shown below in order of DECREASI NG Speed (ie. fastest reaction > intermediate speed reaction > slowest reaction)? Reaction A Reaction B Reaction C Reaction B> Reaction C> Reaction Reaction C> Reaction B> Reaction Reaction A> Reaction C> Reaction OWO>> A B C. Reaction A>Reaction B>Reaction D E Reaction B> Reaction A> Reaction Rationale: Chapter 10 Problem 60 12. 13. Find the major product(s) of the reaction shown below. Ignore stereochemistry. CH3 A + NBS . ? perOXIde CH3 CHZBr CH3 Br 0/ CH3 Br B 1 2 3 4 __ A. 2 and 4 are the major products of this reaction. __ B. 3 is the major product of this reaction. __ C. 3 and 4 are the major products of this reaction. __ D. 1 , 2 , and 5 are the major products of this reaction. __ E. 1 , 3 , and 5 are the major products of this reaction. Rationale: Chapter 12 Problem 26c Choose the CORRECT structure of the product of the reaction shown below. AICI3 + CHz-SCIDH-CH-2CH-ZCIDH-CH3 —> A Cl Cl C' CH CH 3 Cl 4 CH3 5 CI Rationale: moved to Chapter 16 WPOW? Cal-lth Br CH 14- 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 + OH :OH OH l CH3 + (ll CH3 + CH CH CH3 H, JCHs I 3 3 H CH 3 REAC46a CH3\ = B PROD46a H+ —> PROD46b H3C CH3 REAC46.b 'o :'oH :6H :'CH :'oH CH3 CH3 CH3 CH3 CH3 CH3 CH3 H30 CH3 CH3 1 2 3 4 5 W909“? MOON-5h Rationale: Chapter 15 Problem 51 b 15- 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 —> no RO—OR —> 2R0- __ A. The 8—membered ring radical abstracts a hydrogen atom from an ROH molecule. __ B. 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. __ C. The radical on the 8—membered ring attacks a peroxide molecule attaching an OR group to the ring. __ 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 8—membered ring radical abstracts a hydrogen atom from an HCCl3 molecule. Rationale: Chapter 12 Problem 41 10. 11. 12. 13. 14. 15. Answer Key "Grade or Education" CHEM 2261/01 Summer 10 Exam 4 Chapters 10, 11, 14 1 ...
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Summ10Ex4 - "Grade or Education" =1 CHEM...

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