Carbonyl Compound Problems
Extra Problems
9. Draw the following compounds:
a) propionaldehyde b) 2-pentanone c) 2-methylhexanoic acid d) methyl propyl ketone e) 2-methylpentanal
f) acetic acid g) MEK (methyl ethyl ketone) h) acetone i) pentanamide j) butyramide k) ethyl acetate l) acetamide
m) butyl formate n) ethyl ethanoate o) phenyl benzoate p) N-methylbutanamide q) methyl methanoate
10. Name the following compounds:
11. Identify the functional group(s) indicated in each generic IR spectrum.
12. Identify the following carbonyl compounds based on the available spectroscopic data.
a) 1.16 ppm 3H triplet, 2.38 ppm 2H quartet, 11.73 ppm 1H singlet
b) 7.5-7.9 ppm 5H multiplet, 10.02 ppm 1H singlet with the following IR spectrum
13. Draw the products of the following oxidation reactions.
14. Identify an appropriate oxidizing agent to perform the following transformations.
15. Show the products of 1-propyne with each of the following reagents.
a) HgSO4, H2SO4
b) 1) Sia2BH 2) H2O2, OH-
c) 1)O3, 2) Me2S
d) warm, conc. basic KMnO4
16. Identify the reagents necessary to perform the following reactions.
a) 2-butyne to acetic acid (two ways)
b) 1-pentyne to 2-pentanone
c) 1-pentyne to pentanal
d) 2-butyne to 2,3-butanedione
17. Show how you would make the following from an alkene or alkyne and other necessary reagents.
a) 2-butanone
b) butyraldehyde (from an alkyne)
c) propionic acid (two ways, from an alkene and an alkyne)
d) 3,4-heptanedione
e) 2-butanone and butyric acid
f) 2,6-heptanedione
g) propanal and butanal
18. Use 1,3-dithiane to synthesize the following ketones and aldehydes.
a) octanal
b) 3-heptanone
c) methyl ethyl ketone
d) PhCH2CH2CHO
19. Show how you would make the following from an appropriate carboxylic acid and other necessary reagents.
a) 2-butanone
b) 3-hexanone
c) ethyl phenyl ketone
d) benzophenone (Ph(CO)Ph)
20. Show how you would make the following from an appropriate nitrile and other necessary reagents.
a) 2-butanone
b) 3-hexanone
c) ethyl phenyl ketone
d) benzophenone (Ph(CO)Ph)
e) benzoic acid
f) pentanoic acid
21. Show how you would make the following carboxylic acids from a Grignard reagent reacting with carbon dioxide. If the oxidation of an alkyl benzene can be used to synthesize the product, show that reaction as well.
a) 2-methylbutanoic acid
b) benzoic acid
c) 2-methylpropanoic acid
d) hexanoic acid
e) p-nitrobenzoic acid
22. There are two alkenes, each one contains only one double bond, that react with a hot, concentrated, basic solution of KMnO4 to make acetic acid (ethanoic acid) as the only organic product. What are these two alkenes?
23. It is possible, through a series of reactions, to turn toluene (PhCH3) into phenylacetic acid (PhCH2CO2H). Show one pathway using NBS and making a Grignard reagent. Can you find more than one way to do this?
24. a) Show how you would make 5-nonanone by using bromobutane as the only organic reagent. For one reaction, turn bromobutane into CH3CH2CH2CH2CN. For the other, turn bromobutane into butyl Grignard. Then, perform any other necessary reactions.
b) What would be the product of the acid hydrolysis of the pentane nitrile intermediate?
25. a) What is the product of 1-methyl-1-cyclopentanol reacted with concentrated sulfuric acid and heat?
b) What is the product when the answer from a) is reacted with ozone followed by Me2S.
c) What is the product when the answer from part a) is reacted with OsO4/H2O2, then HIO4?
26. List three (or more) ways to synthesize pentanoic acid.
27. Provide the major organic products for the following reactions.
28. Fill in the blanks in the following reactions.
29. Describe the reagents that could be used to perform the following reactions. Sometimes, more than one reaction may be required.
30. Show how the following compounds can be synthesized from an appropriate carboxylic acid. For the aldehydes, provide two syntheses, one with an ester intermediate and one with an acid chloride intermediate.
