Amine, Nitrile Problems
Extra Problems
15. Draw the following compounds.
a) 1,4-dicyanocyclooctane
b) 2-methylheptanenitrile
c) 3-aminocyclopentanone
d) m-nitroaniline
e) 3-methylpyridine
f) diethylamine
g) 3-octanamine
h) N-methyl-2-butanamine
16. Name the following compounds.gents/products for the following reactions.
17. Identify the functional group(s) indicated in each generic IR spectrum between a primary amine, a secondary amine, a nitrile, and an amide. Additionally, which contains a phenyl ring?
18. Describe how IR spectroscopy could be used to distinguish between triethylamine, diethylamine, and ethylamine.
19. What is the key feature of the M+ peak in a mass spectrum that indicates the compound has an odd number of nitrogen atoms in it?
20. Draw the products of the following reactions.
21. Provide an appropriate reagent to perform the following transformations.
22. Draw the products of the following reductions.
a) PhCH2CN + LiAlH4
b) PhCH2CONH2 + LAH
c) PhCH2C=NH + LiAlH4
d) benzonitrile + LiAlH4
e) PhCONHPh + LiAlH4
f) m-nitroaniline + Fe/HCl followed by NaOH
23. Fill in the reagents to perform the following reactions.
24. Draw the amides synthesized from the following reactions.
a) PhCOCl + excess ethylamine
b) benzoic acid + methylamine
c) propanoic acid + aniline
d) pentanoic acid + SOCl2 followed by excess 2-aminobutane
e) CH3CH=CHCH2CO2H + ammonia (NH3)
f) butyric acid + thionyl chloride followed by excess propylamine
g) PhCH2CO2CH3 + H2NCH3
25. Draw appropriate carboxylic acids and amines that can synthesize the following amides.
26. Provide appropriate acid chlorides and amines that can synthesize the following amides.
27. The following peptide was synthesized from several amino acids.
a) How many?
b) Draw out all of the amino acids used to make this peptide.
28. Provide the appropriate amines that could be used as reagents in the following reactions.
29. Draw the acid hydrolysis product of each of the following compounds.
30. Draw the products of the following reactions.
31. Show how you would synthesize the following products starting from a nitrile compound.
a) benzoic acid
b) benzophenone (PhCOPh)
c) 3-heptanone
d) pentanamine
e) 2-methylpentanoic acid
f) cyclohexylmethylketone
g) acetic acid
h) PhCH2NH2
i) acetone
j) butyric acid
k) ethylamine