CHE 325 ALDEHYDES AND KETONES I CHAP 18 ASSIGN OCH 3 HCN C 4 H 7 NO. would be: CH 3 B. CH 3CH 2COOCH 3

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1 CE 325 ALDEYDES AND KETNES I CAP 18 ASSIGN 1. What is the correct IUPAC name for the following compound A. 2-Methyl-5-heptanone B. 7-Methyl-4-octanone C. 6-Isopropyl-4-octanone D. Isobutyl propyl ketone E. 1,1-Dimethyl-4-heptanone 2. Which is the proper name for the structure shown A. 3,5-Dimethyl-5-(4-chlorobenzyl)-1-pentanal B. 3-Methyl-5-(4-chlorophenyl)hexanol C. 3,5-Dimethyl-5-(4-chlorophenyl)-1-pentanaldehyde D. 3-Methyl-5-(4-chlorophenyl)-hexanaldehyde E. 3-Methyl-5-(4-chlorophenyl)hexanal Cl 3. Which of the following compounds is an acetal A. I B. II C. III D. IV E. None of these I II III IV 4. The product, C, of the following reaction sequence, C + CN CN C 4 7 N 2 2 S 4 heat C would be: A. C 2 CC B. C 2C C C. E. None of these CN D. C=CC 5. What new compound will be formed when Cl is added to a solution of pentanal in methanol Cl Cl A B C D E 6. Select the structure of the major product in the following reaction. A. Ethylbenzene B. 1-Phenylethanol C. Acetophenone D. 2-Phenylethanal E. Vinylbenzene 2 S 4 gs 4, 2 1 P a g e

2 7. The product,, of the following reaction sequence, C 6 5 C 2 Br + (C 6 5 ) 3 P would be: F C 6 5 Li G C 6 5 C C 6 5 C 2 CC 6 5 A. B. C 6 5 C 2 CC 6 5 C 6 5 C CCC 6 5 C. D. C 6 5C 2C=CC 6 5 C 6 5 C C E. C Select the structure of the major product in the following reaction. A. Ethylbenzene B. 1-Phenylethanol C. Acetophenone D. 2-Phenylethanal E. Vinylbenzene i) B 3 ii) 2 2, -, 2 9. Which of the compounds listed below would you expect to have the highest boiling point (They all have approximately the same molecular weight.) A. pentane B. 1-butanol C. Butanal D. 1-fluorobutane E. diethyl 10. The product, K, of the following sequence of reactions Benzene C 2 MgBr 3 I J + AlCl 3 CCCl K would be: 11. The product, E, of the following reaction sequence, C 2 C PCl 5 C 6 6 NaB 4 C D E AlCl 3 would be: C 2 C 2 CC 2 CC 2 CC 2 C( ) 2 2 P a g e

3 12. Predict the major organic product of the following reaction: Ag(N 3 ) C 3 C 3 C 3 C 13. Select the structure of the major product in the following reaction. A. 4-methylhexanal B. 4-methyl-1-hexanol C. 3-methylhexanal D. 4,10-dimethyldodecane-6,7-dione E. 4,10-dimethyldodecane-6,7-diol i) 2, Lindlar catalyst ii) 3 iii)zn, C Reaction of which of the following compounds with aqueous base results in an aldehyde A. C 2C 2Cl B. CClC 2Cl C. C=CCl 2 D. C 2CCl 2 E. CCl Which reagent will not differentiate between 3-butenal and 2-butanone A. Br 2/CCl 4 B. Ag 2, - C. 2NNC 6 5 D. KMn 4, E. None of these 16. The product, J, of the following reaction sequence, CC SCl 2 ( ) 2 CuLi I CCCu J would be: CC C C CC CCC A B C D E 17. What is the product of the following reaction sequence PCC C 6 5 C 2 C 2 Cl 2 BrC 2 C 2 Et, Zn benzene 3 + A. C 6 5C 2C 2C 2Et B. C 6 5 CC 2 C 2 Et C. C 6 5 CC 2 C 2 Et E. C 6 5C 2C 2C 2Et D. C 6 5 CC 2 C 2 Et 3 P a g e

4 18. What is the major product of the following reaction sequence A. I B. II C. III D. IV E. V i), Cl ii) LA, Et 2 iii) 2, 3 + I II III IV V 19. What, in general, is the order of decreasing reactivity of these carbonyl compounds towards nucleophilic reagents C C ( ) 3 CC C ( ) 3 CCC( ) 3 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 20. The Baeyer-Villiger oxidation of propiophenone (ethyl phenyl ketone) produces chiefly: A C 2 CC 6 5 C. p-c 6 4 CC 2 B. C 2 CC 6 5 D. C 6 5 CC 2 E. C 6 5 CC 2 C What is the final product, Z, of the following synthesis 1. LiAl(-t-Bu) 3 1. KMn 4, -, heat SCl 2, -78 o C X Y Z CAl(t-Bu) 2 C C CLi C 4 P a g e

5 22. What is the reactant W in the synthesis given below A. Cyclopentanone B. Cyclopentene C. Cyclopentanol D. Bromocyclopentane E. Triphenylphosphine oxide Cl + V (C 6 5 ) 3 P + W C 6 5 Li Wittig reagent 23. What is the final product of this synthetic sequence Benzene Br 2 FeCl 3 Mg 1. C 6 5 C 2 Cr acetone A. C 6 5 CC 6 5 B. p-brc 6 4C 2C 6 5 C. C 6 5C 2C D. C 6 5 C 2 CC 6 5 E. C 6 5C 2C Which of the reactions listed below would serve as a synthesis of acetophenone, C 6 5 C A. C 6 5 CCl + ( ) 2 CuLi B. C CCl C. C 6 5 CN + Li D. Answers A) and B) only E. Answers A), B), and C) AlCl ow could the following synthetic conversion be accomplished C 2 C 2 C C 2 C A. gs 4/ 2S 4; then PCl 5/0 C; then NaN 2, liq. N 3 B. PCl 5/0 C; then NaN 2, liq. N 3; then Sia 2B; then 2 2 C. PCl 5/0 C; then NaN 2, liq. N 3; then gs 4, 2S 4/ 2 D. NaN 2, liq. N 3; then PCl 5/0 C; then gs 4, 2S 4/ 2 E. 2 2; then PCl 5/0 C; then NaN 2, liq. N 3; then Sia 2B 5 P a g e

6 26. The following reduction can be carried out with which reagent(s) A. Zn(g), Cl B. i) SC 2C 2S, BF 3 ; ii)raney Ni ( 2) C. NaB 4, D. A & B E. A & C 27. The relationship of 3-methyl-2-heptanone and 3-methyl-2-hepten-2-ol is designated by the term: A. tautomers B. conformational isomers C. diastereomers D. resonance structures E. stereoisomers 28. The 1 NMR spectrum of a compound with formula C 7 14 gives a doublet at 9.2 ppm. Which of these structures is a possible one for this compound A. 2-methyl-3-hexanone B. 2-methylhexanal C. 2,2 -dimethylpentanal D. 2,2-dimethyl-3-pentanone E. two of the above 29. Which of the following can exist as stereoisomers A. the hydrazone of butanone B. the oxime of acetone C. the phenylhydrazone of cyclohexanone D. the cyclic acetal formed from propanal and ethane-1,2-diol E. the imine of cyclopentanone 30. Which of the following procedures would not yield () 2 CC A. I B. II C. III D. IV E. V I II III C 2 as a product PCC C 2 Cl 2 SCl 2 3 LiAl(-t-Bu) 3, -78 o C Zn Ac IV KMn 4 Na 3 + V P a g e

7 31. Which of the following is a synthesis of 3-heptanone PCC 1. C 2 MgBr 2 Cr 2 4 C 2 C 2 C 2 C 2 A. C 2 Cl acetone (C 2 ) 2 C 2 Li 3 + C 2 CN B. PBr 3 NaCN C 2 MgBr 3 + C 2 C 2 C 2 C. C 2 C 2 C 2 C 2 KMn C 2 Li 2 D. -, E. All of the above are syntheses of 3-heptanone. 32. A compound with formula C 5 10 gives two signals only, both singlets, in the 1 NMR spectrum. Which of these structures is a possible one for this compound A. C 2 CC 2 B. () 2 CC C 2 CC C. () 3 CC E. () 2 CC 2 C D. 33. Which of the following is formed when 3-methylcyclopentanone reacts with semicarbazide A. I B. II C. III D. IV N-N-C 6 5 N-N 2 N- E. V I II III N N N 2 N N N 2 N 2 IV V 7 P a g e

8 NAME DATE ANSWER SEET CE 325 CAP 18 ASSIGN SS II P a g e