FINALexam

FINALexam - Name: _ Last four numbers of the ID: _ Part A...

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Page 1 Name: ____________________________ Last four numbers of the ID: _____________ Part A 1. The IR spectrum of which type of compound will not show evidence of hydrogen bonding? A) Aldehyde B) Alcohol C) Carboxylic acid D) Phenol E) Primary amine 2. LiAlH 4 (LAH) cannot be used to convert carboxylic acids to the corresponding aldehydes because: A) LAH is not sufficiently reactive. B) RCOOH is converted into RCOOLi. C) LAH is too reactive and RCOOH is reduced to RCH 2 OH. D) RCOOH is reduced to RCH 3 . E) RCOOH is converted into R 2 C=O. 3. A compound with formula C 5 H 10 O gives two signals only, both singlets , in the 1 H NMR spectrum. Which of these structures is a possible one for this compound? A) CH 3 CH 2 CCH 2 CH 3 O B) (CH 3 ) 2 CHCCH 3 O C) (CH 3 ) 3 CC O H D) CH 3 CH 2 CHC O H CH 3 E) (CH 3 ) 2 CHCH 2 CO H Page 2 4. What is the final product, Z, of the following synthesis? CH 3 COAl( t -Bu) 2 O COCH 3 O CH O COLi O COH O 1. KMnO 4 , OH - , heat 2. H 3 O + SOCl 2 1. LiAlH(O- t -Bu) 3 ether, -78 o C 2. H 2 O XY II I I I I I V V CH 2 OH A) I B) II C) III D) IV E) V 5. An aldehyde results from the reaction of which of these compounds with aqueous base? A) CH 3 CH 2 CH 2 Cl B) CH 3 CHClCH 2 Cl C) CH 3 CH=CCl 2 D) CH 3 CH 2 CHCl 2 E) CH 3 CCl 2 CH 3 6. The product, K, of the following sequence of reactions I CH 3 CH 2 MgBr ether J Benzene CH 3 CHCOCl K CH 3 AlCl 3 H 3 O + would be: OH HO O OH O I I I I I V V A) I B) II C) III D) IV E) V
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Page 3 7. What, in general, is the order of decreasing reactivity of these carbonyl compounds towards nucleophilic reagents? CH 3 CCH 3 CH 3 CO (CH 3 ) 3 CCCH 3 HC O (CH 3 ) 3 CCC(CH 3 ) 3 O H O O H II I I I I I V V A) I > III > V > II > IV B) IV > II > I > III > V C) V > III > I > II > IV D) II > I > V > III > IV E) III > V > IV > II > I 8. The compound C 6 H 5 -CH=N-NH 2 is produced by the reaction of benzaldehyde with which compound? A) Ammonia B) Hydrazine C) Nitrogen D) Phenylhydrazine E) Hydroxylamine 9. What is the major product of the following reaction sequence? OCH 3 O O I I OH HO HO O OH O O IV V i) ii) LAH, Et 2 O iii) H 2 O, H 3 O + ? OH O OH O HO OH , HCl A) I B) II C) III D) IV E) V Page 4 10. The aldol cyclization of CH 3 CCH 2 CH 2 CH 2 C=O O H produces which of these? I I I V C O CH 3 C=O H O C=O H O O O CH 3 CH 3 V A) I B) II C) III D) IV E) V 11. Which of these compounds would have the lowest pKa?
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FINALexam - Name: _ Last four numbers of the ID: _ Part A...

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