i. NaCN ii. 70% H 2 SO 4, reflux

Transcription

1 CHE 325 CARBXYLIC ACID CHAP 18 AIGN 1. In which of the following sequences are the compounds listed in order of decreasing acidity? A. CH 3CH > H 2 > CH 3CH 2H > HC CH > NH 3 B. CH 3CH 2H > CH 3CH > H 2 > HC CH > NH 3 C. CH 3CH > CH 3CH 2H > H 2 > NH 3 > HC CH D. H 2 > CH 3CH > CH 3CH 2H > HC CH > NH 3 E. CH 3CH 2H > H 2 > CH 3CH > HC CH > NH 3 2. Which of the following would be the strongest acid? E. I C 2 H II C 2 H III C 2 H C 2 H C 2 H I 3. Which reagent would best serve as a basis for a simple chemical test to distinguish between CH 3CH 2CH and CH 3CCH 3? A. conc. H 2 4 B. Br 2/C 4 C. Cr 3/H 2 4 D. NaHC 3/H 2 E. KMn 4/H 2 4. What is the expected product, A, of the following reaction sequence? A. HC 2CH 2C 6H 5 B. C 6H 5CH 2CH C. C 6H 5CH 2 3H D. C 6H 5CHCH E. =C(CH 2C 6H 5) 2 i. NaCN ii. 70% H 2 4, reflux A + NH What would be the final product? A. C 6H 5CH 2C 2CH 3 B. C 6H 5CH 2CH 2NHCH 3 C. C 6H 5CH 2CCH 3 D. C 6H 5CH 2CH(CH 3)CN E. C 6H 5CH 2CH=NCH 3 C 6 H 5 CH 2 CNH 2 P 4 H 10 heat i. CH 3 MgI, Et 2 ii. H 3 +? 6. Predict the final product likely to be obtained when ()-2-methyl-3-pentanol is subjected to the following sequence of reactions: i) Tosyl chloride; ii) NaH (aq), heat A. ()-2-methyl-3-pentanol B. (R)-2-methyl-3-pentanol C. (R, )-2-methyl-3-pentanol D. 2-methyl-2-pentene E. (R, )-2-methyl-3-pentanol and 2-methyl-2-pentene in more or less equal amounts 7. Which of the following compounds is capable of forming a -lactone? A. 5-hydroxypentanoic acid B. pentanedioic acid C. 4-hydroxypentanoic acid D. 3-hydroxypentanoic acid E. 2-hydroxypentanoic acid 1

2 8. Predict the major organic product of the following reaction sequence: E. H H heat H + KMn 3 + 4? H 2, H C 2 H CH I II III H CH I 9. What would be the product of the following reaction? E. H 18 + H? HA I II III 18 II III 10. What would be the final organic product of the following reaction? A. (CH 3) 3CC 2H B. (CH 3) 3CCCH 3 C. (CH 3) 3CCH 2H D. (CH 3) 3CCH 3 E. (CH 3) 3CC 2CH 3 Br i. Mg, Et 2 i. LAH, Et 2 ii. C 2 ii. H 2? iii. H Which reactant is unlikely to produce the indicated product upon strong heating? A. 2,2-dimethylpropanedioic acid 2-methylpropanoic acid B. 2-ethylpropanedioic acid butanoic acid C. 2-methyl-3-oxo-pentanoic acid 3-pentanone D. 2-methyl-4-oxo-pentanoic acid 2-methyl-3-butanone E. 4-methyl-3-oxo-heptanoic acid 3-methyl-2-hexanone 2

3 12. Identify the product(s) of the following reaction. E. C 2 H heat? H I II III + C 2 C 2 H + C 2 C 2 H I 13. What is the final product obtained when toluene is subjected to the following reaction sequence? i) 2 (large excess), heat, h ; ii) H /H 2, heat; iii) H 3 + H H H E. I II III H I C 3 C 2 H H H C Rank the following in order of relative acidity (more acidic > less acidic). A. B > C > A > D B. C > A > D > B C. D > C > A > B D. C > D > A > B E. B > A > D > C 15. Which of the following would serve as syntheses of (CH 3) 3CC 2H? i. 2 /H (excess) ii. H 3 + Br i. CN ii. H 3 + (heat) A B C D. Answers A and B only E. Answers A and C only Br i. Mg, Et 2 ii. C 2 iii. H 3 + 3

4 16. Which of the following would yield ()-2-butanol? (R)-2-Bromobutane i. CH 3 C 2 Na + (R)-2-Bromobutane ii. H, H 2, heat H, H 2, heat ()-sec-butyl acetate H, H 2, heat A B C D. All of these E. None of these 17. Which of the following is not a method for preparing butanoic acid? A. CH 3CH 2CH 2Br + NaCN; then H 3 +, reflux B. CH 3CH 2CH 2MgBr + C 2; then H 3 + C. CH 3CH 2CH 2H + C D. CH 3CH 2CH 2C 2Et + H /H 2; then H 3 + E. CH 3CH 2CH 2CH 2H + KMn 4/H /H 2/heat; then H Which of these combinations will not produce benzoic acid? A. C 6H 5CH 2H + KMn 4/H /H 2, heat; then H 3 + B. C 6H 5CH 3 + KMn 4/H /H 2, heat; then H 3 + C. C 6H 6 + C 2, high pressure D. C 6H 5CCH 3 + 2/H /H 2; then H 3 + E. C 6H 5C + H /H 2; then H Which of the following statements concerning nitriles is incorrect? A. Nitriles can be hydrolyzed to carboxylic acids. B. Nitriles can be formed from (many) alkyl halides by nucleophilic substitution by cyanide ion. C. Nitriles can be reduced with excess lithium aluminum hydride to primary amines, RNH 2. D. Nitriles react with Grignard reagents to form tertiary alcohols. E. Nitriles can be made by the dehydration of amides. 20. What is the IUPAC name of the following compound? A. 4-hydroxy-3-methylbutanoic acid B. 3-hydroxy-2-methylbutanoic acid C. 1-hydroxy-2-methylbutanoic acid D. 3-(hydroxymethyl)butanoic acid 21. The cleansing action of soaps is due to the formation of A. water insoluble micelles with lipophilic interiors. B. water soluble micelles with lipophilic interiors. C. water insoluble micelles with hydrophilic interiors. D. water soluble micelles with hydrophilic interiors. 22. What is the product of the reaction shown below? 4

5 23. Which of the following undergo decarboxylation upon heating? and I B. I and III C. II and III D. III and I 24. nly one of the reaction sequences below can carry out the following transformation. Identify which reaction sequence it is. 25. Which of the reactions below would not proceed as shown? A. B. C. D. E. 26. What is the correct IUPAC name for the following molecule? A. 6-Bromo-7-hydroxy-3-methylnonanoic acid B. 4-Bromo-3-hydroxy-7-methyl-9-nonanoic acid C. (3,6R,7 )-6-Bromo-7-hydroxy-3-methylnonanoic acid D. (3,6R,7R )-6-Bromo-7-hydroxy-3-methylnonanoic acid E. (3,4R,7 )-4-Bromo-3-hydroxy-7-methyl-9-nonanoic acid 5

6 EXTRA CREDIT 27. Which of the following is not formed as either a product or intermediate during the course of the reaction shown below? A B C D E 28. Reasoning by analogy, one would predict that the reaction of carbon disulfide with sec-butylmagnesium bromide should yield which of the following (after acidification)? E. I I II III NAME DATE ANWER EET CHE 325 CHAP 18 AIGN II