ALDEHYDES AND KETONES

Transcription

1 CE 325 ALDEYDES AND KETNES CAP 17 ASSGN NUCLEPLC ADDTN T TE CARBNYL GRUP 1. What is the correct UPAC name for the following compound A. 2-Methyl-5-heptanone B. 7-Methyl-4-octanone C. 6-sopropyl-4-octanone D. sobutyl propyl ketone E. 1,1-Dimethyl-4-heptanone 2. A correct name for C 6 5 C 2 C 2 C is A. 3-Benzylpropanone B. 3-Phenylpropanal C. 3-Benzylpropanal D. Nonanone E. Nonanal 3. 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 4. Which of the following compounds is an acetal A. B. C. D. V E. None of these C 3 V 5. Which is the general formula for a thioacetal RCSR' RCSR' RCSR' RCR' RC S S SR' SR' A B C D E 6. The product, C, of the following reaction sequence, C 3 CC 3 + CN CN C 4 7 N 2 2 S 4 heat C would be: C 3 A. C 2 CC B. C 3C 2CC 3 C 3 CC 3 C. CN D. C 3C=CC E. None of these 1

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 CC 3 C 3 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 CC 3 E. C What would be the product of the following reaction sequence A. B. C. D. V E. V i) PCl 3 ii) C 6 6, AlCl 3 iii) Zn(g), Cl, heat V V 9. What new compound will be formed when Cl is added to a solution of pentanal in methanol Cl Cl A B C D E 10. 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 2

3 11. The product, K, of the following sequence of reactions C 3 Benzene C 3 C 2 MgBr 3 J + AlCl 3 C 3 CCCl K would be: A. B. C. D. V E. V 12. Predict the major organic product of the following reaction: Ag(N 3 ) C 3 C 3 C 3 C A. B. C. D. V E. V 13. The product, E, of the following reaction sequence, C 3 C 2 C PCl 5 C 6 6 NaB 4 C D E AlCl 3 C 3 would be: C 2 C 2 C 3 CC 2 C 3 CC 2 C 3 CC 2 C 3 C(C 3 ) 2 A. B. C. D. V E. V 14. 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, -, 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 3 C 2 3

4 16. The product, J, of the following reaction sequence, C 3 CC SCl 2 C 3 (C 3 ) 2 CuLi J would be: C 3 CCCu C 3 CCC 3 C 3 C CC 3 C 3 C 3 CCC 3 C 3 CCCC 3 C 3 C 3 C 3 C 3 C 3 A B C D E 17. What is the major product of the following reaction sequence A. B. C. D. V E. V C 3 i), Cl ii) LA, Et 2 iii) 2, 3 + V V 18. An aldehyde results from the reaction of which of these compounds with aqueous base A. C 3C 2C 2Cl B. C 3CClC 2Cl C. C 3C=CCl 2 D. C 3C 2CCl 2 E. C 3CCl 2C 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 20. The Baeyer-Villiger oxidation of propiophenone (ethyl phenyl ketone) produces chiefly: A C 3 C 2 CC 6 5 B. C. p-c 6 4 CC 2 C 3 D. C 3 C 2 CC 6 5 C 6 5 CC 2 C 3 E. C 6 5 CC 2 C 2 4

5 21. 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 22. What, in general, is the order of decreasing reactivity of these carbonyl compounds towards nucleophilic reagents C 3 CC 3 C 3 C (C 3 ) 3 CCC 3 C (C 3 ) 3 CCC(C 3 ) 3 A. > > V > > V B. V > > > > V C. V > > > > V D. > > V > > V E. > V > V > > 23. What is the final product, Z, of the following synthesis C 3 1. LiAl(-t-Bu) 3 1. KMn 4, -, heat SCl 2, -78 o C X Y Z CAl(t-Bu) 2 CC 3 C CLi C A. B. C. D. V E. V 24. What is the final product of this synthetic sequence Benzene Br 2 Mg FeCl 3 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 6 5 5

6 25. Which of the reactions listed below would serve as a synthesis of acetophenone, A. B. C 6 5 CCl + (C 3 ) 2 CuLi C C 3 CCl C. C 6 5 CN + C 3 Li D. Answers A) and B) only E. Answers A), B), and C) AlCl C 6 5 CC 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, C 3 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 compound C 6 5 C N N CC 6 5 is produced by the reaction of an excess of benzaldehyde with which compound A. Ammonia B. ydrazine C. Nitrogen D. Phenylhydrazine E. ydroxylamine 29. Which of the following procedures would not yield (C 3 ) 2 CC as a product A. B. C. D. V E. V C 2 PCC C 2 Cl 2 SCl 2 3 LiAl(-t-Bu) 3, -78 o C Zn Ac V KMn 4 Na 3 + V 3 + 6

7 30. Which of the following is a synthesis of 3-heptanone PCC 1. C 3 C 2 MgBr 2 Cr 2 4 C 3 C 2 C 2 C 2 C 2 A. C 2 Cl acetone C 3 (C 2 ) 2 C 2 Li 3 + C 3 C 2 CN B. PBr 3 NaCN C 3 C 2 MgBr 3 + C 3 C 2 C 2 C 2 C. C 3 C 2 C 2 C 2 C 2 KMn C 3 C 2 Li 2 D. -, E. All of the above are syntheses of 3-heptanone. 31. Which of the following is formed when 3-methylcyclopentanone reacts with semicarbazide A. B. C. D. V E. V N-N-C 6 5 N-N 2 N- N N N 2 N N N 2 N 2 V V 32. 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 33. 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 3 C 2 CC 2 C 3 B. (C 3 ) 2 CCC 3 C 3 C 2 CC C. (C 3 ) 3 CC D. C 3 E. (C 3 ) 2 CC 2 C 34. The 13 C NMR spectrum of a compound with formula C 7 14 gives three signals. Which of these structures is a possible one for this compound A. 2-heptanone B. 3-heptanone C. 2,2-dimethyl-3-pentanone D. 2,4-dimethyl-3-pentanone E. two of the above 7

8 35. Which of the following compounds most likely generated the accompanying 1 NMR-spectrum A B C D E 36. To which side, if any, would the following equilibrium lie A. To the right. B. To the left. C. Equally to the right and left. D. There is no way to predict this. E. This reaction cannot occur. EXTRA CREDT 37. Stereoisomers can exist in the case of which of the following 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 38. ow could the following synthetic conversion be accomplished 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 C 3 C 2 C 2 C C 3 C 2 CC 3 8

9 NAME DATE ANSWER SEET CE 325 CAP 17 ASSGN SS