Skip to the lesson

22.8 Amine, Nitrile Problems

22.7 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.

Problem 16, amine & nitrile problems

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?

Problem 17, amine & nitrile problems

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.

Problem 20, amine & nitrile problems

21. Provide an appropriate reagent to perform the following transformations.

Problem 21, amine & nitrile problems

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.

Problem 23, amine & nitrile problems

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.

Problem 25, amine & nitrile problems

26. Provide appropriate acid chlorides and amines that can synthesize the following amides.

Problem 26, amine & nitrile problems

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.

Problem 27, amine & nitrile problems

28. Provide the appropriate amines that could be used as reagents in the following reactions.

Problem 28, amine & nitrile problems

29. Draw the acid hydrolysis product of each of the following compounds.

Problem 29, amine & nitrile problems

30. Draw the products of the following reactions.

Problem 30, amine & nitrile problems

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