Summ08Ex4

Summ08Ex4 - "Grade or Education" =1 CHEM...

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Unformatted text preview: "Grade or Education" =1 CHEM 2261/01 Summer 08 Exam 4 Chapters 10, 11, 14 1 . Choose the CORRECT statement from the multiple choices concerning compounds with the numbered structures shown below. CH2OH CH-ZCHZOH OH OH 1 g Q A H30 OH CH3 (PH (PH i .OH : .CH-CH3 : CH-CH3 § § 2 § __ A. Q will undergo dehydration more rapidly than i when heated with H2504. __ B. Q will undergo dehydration more rapidly than 1 when heated with H2504. __ C. 1_ will undergo dehydration more rapidly than 1 when heated with H2504. __ D. 1 will undergo dehydration more rapidly than i when heated with H2504. __ E. 1 will undergo dehydration more rapidly than Q when heated with H2504. Rationale: similar to Chapter 10 Problem 34(a—e) 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. CH'SCIEH'CH'ZOH CHQH'CH'ZCH'ZCH'ZOH CH3 CH3 0 l? 1‘? IO /\ _ _ _ _ _ H2C_CH2 H3C4©7fi CI R OOH H3C C CI CH3CHZOCHZCH3 0 E0 TSCI RCO3H ACCI Et20 A First: TsCl /pyridine; Next: CH2=CHMgBr; Next: RCO3H; Finally: H+/HZO B. First: TsCl /pyridine; Next: EO; Finally: HO'/HZO C. First: HBr/A; Next: Mg/EtZO; Finally: 1. EO, and 2. H+ D First: HBr; Next: Mg/EtZO; Next: AcCl ; Finally: HZ/Pd E First: TsCl /pyridine; Next: HOCHZCHZMgBr Rationale: Chapter 1 1Problem 25b How many alkyl chlorides can be obtained from monochlorination of the hydrocarbon whose structure is shown below? Disregard stereoisomers. CH 3 WPOW? \ICDw-bU'I Rationale: Chapter 12 Problem 4e 4- Choose structure of the ma'or product of the reaction shown below. CH peroxide Br CH CH3 3 CH3 CH3 CH3 Br Br Br Br 1 2 § 5 § __ A. i __ B. i __ C. ; __ D. 1_ __ E. ; Rationale: Chapter 12 Problem 32e 5. Choose structure of the ma'or product of the reaction shown below. w w CHZBr 1 __ A. 1 __ B. i __ C. 1_ __ D. i __ E. ; Rationale: Chapter 12 Problem 26e CH CH 3 CH3 2 3 + NBS CH3 Br CH3 Br CH3 g A peroxide Br CH3 >2 Br CH3 5 CH IU'I CH 5- Choose structure of the product(s) of the reaction shown below. 3 CHZCIZ + CI2 —> ? hv HC CHeCI 3 CI CH3 CH3 6 d d. @ CI 1 2 § 5 This reaction produces only product i. This reaction produces only product ;. A B C. This reaction produces only product 1_. D This reaction produces only product i. E This reaction produces products 1_, g, i, and i. Rationale: Chapter 12 Problem 22f 7. Figure out the names of the five compounds whose structures are shown below. Choose the one which is CORRECTLY named in the multiple choices. 00 H3 CH3 CHIC H2 0H (3 (j [j (j 1 2 3 4 5 Compound 1_ is phenol. Compound 1 is benzaldehyde. A B C. Compound; is benzonitrile. D Compound i is toluene. E Compound ; is anisole. Rationale: Chapter 15 Problem 35 8- 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: Bra/hv; Next: Mg/EtZO; Next: EO; Finally: H+/HZO B First: Bra/hv; Next: tert —BuO '; Next: BrZ/CHZCIZ; Next NaNHZ (excess); Finally: H+/H;,~_O C. First: Bra/hv; Next: tert —BuO '; Next: RCO3H; Finally: HO' D First: Bra/hv; Next: tert —BuO '; Next: EO; Finally: HO' E First: Bra/hv; Next: HO'; Next: HZCrO4; Next: RC03H; Finally: HO' Rationale: Chapter 1 2 Problem 19d 9. 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.) + CH2 Q v + 1 IN IOO IU'I ; is nonaromatic. i is antiaromatic. i is nonaromatic. 1_ is antiaromatic. ; is aromatic. Rationale: Chapter 15 Problem 36 10- By looking at the numbered structures below figure out which of the multiple choices specifies the CORRECT product of a reaction. 0 O OH II CH-ZCHZOH CH-Zc-OH U U 1 2 3 4 I? HO-CH2 OCH3 CH30'CH2 OH § § 1 1_ + H+/CH30H —> g 1_ + H+/CH30H —> 1 __ A. __ B. __ C. + CH30'/CH30H —> Q __ D. __ E. Rationale: Chapter 10 Problem 38(d,e,f,i) 11. Work out the curved—arrow mechanism for the rearrangement reaction shown below. OH O W Which of the numbered curved—arrow mechanistic processes shown below is NOT part of your mechanism? OH W 1 5 H2804 H20 HO HO loo + A. @4- HQH W HO § __ A. 1_ __ B. 1 __ C. i __ D. g __ E. i Rationale: Chapter 10 Problem 59a 1 2- Choose the CORRECT structure of the product of the reaction shown below. AICI3 + CHéCIDH-CH-ZCH-ZCIDH-CHS —> ? CI CI A CI CH3 CH3 CI 1 C|H3 2 CH3 CI § CH3 A CH3 § CI __A. 1 __B. ; __C. i __D. 1_ __E. 5 Rationale: moved to Chapter 16 13. 14. Choose number of the CORRECT structure of the product of the following reaction: 1. NBS/Alperoxide 2. ' CEN CH3 3. H2/Ni _, 7 Br I : CHZNHZ: ,CH-ZCH2NH2 : ,CH-NH2 : ,CH-ZCN : ,CN 1 2 3 4 5 A 1_ B. i __ C. i D 1 E i Rationale: moved to Chapter 16 Choose the alkyl halides which could SUCCESSFULLY numbered structures below. be used to make Grignard reagents from the O H CH3 1 2 g 5 __ A. The alkyl halides with structures 1 and i could be successfully used to make Grignard reagents. __ B. Only the alkyl halide with structure 1 could be successfully used to make a Grignard reagent. __ C. All four alkyl halides could be used successfully to make Grignard reagents. __ D. The alkyl halides with structures 1_ and ; could be successfully used to make Grignard reagents. __ E. None of the alkyl halides shown could be used successfully to make Grignard reagents. Rationale: similar to Chapter 1 1 Problem 23 1O 15. Work out the curved—arrow mechanism for the rearrangement reaction shown below. Which of the numbered curved—arrow mechanistic processes shown below is NOT part of your mechanism? CH3 | : /CH-ZCH-2CH-CH=CH2 H+ H3C CHECH3 (EH3 A + 9H3 CH'2CH'2CH-CHZCH2 H CH-ZCH-2CID— H-CH3 H 1 + CH3 — CH'2CH3 _ 9H3 § 82 CIDH3 5 E __A. i __B. i __C. 1_ __D. i __E. ; Rationale: Chapter 15 Problem 47a 11 10. 11. 12. 13. 14. 15. Answer Key "Grade or Education" CHEM 2261/01 Summer 08 Exam 4 Chapters 10, 11, 14 1 12 ...
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Summ08Ex4 - "Grade or Education" =1 CHEM...

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