Amines Solutions 97

  1. Give the IUPAC name and where possible, the common name of the following:

a)
(I) N-isopropyl-2,2-dimethyl-1-propanamine
(c) isopropylneopentylamine


b)
(I) 2-butanamine
(c) sec-butylamine


c)
(I) N-methyl-N-propylcyclohexanamine
(c) cyclohexylmethylpropylamine


d)
(I) 2-cyclopentylethanamine


e)
(I) phenylmethanamine
(c) benzylamine

  1. Draw structures of the following compounds:

a)3-aminobutanal

b)3-bromopyridine

c)2-aminopyrrole

d)N-methylpyrrolidine

e) tert-butylethylisopropylammonium hydroxide

  1. Give the approximate pKb of

a)an alkyl amine such as methylamine3 - 4

b)an aromatic amine such as aniline9 - 10

  1. Write equations to show how the following amine can be synthesized from a suitable alkyl halide. Show all reagents and catalysts and any intermediate products. Mechanisms are not required. More than one step may be required.

a)using sodium azide

b)using sodium cyanide

  1. Draw the structures of the reagents needed to prepare the following amines by reductive amination of an aldehyde and if possible a ketone. Show all possible sets of reagents.
  2. Write equations showing all the reagents needed and any intermediate products formed producing t-butylamine by

a)Hoffman rearrangement

b)Curtius rearrangement

  1. Write equations showing the Hoffman elimination of the following compound. Show all reagents and the major alkene product

  1. Write equations, including all reagents and catalysts, showing how p-bromoiodobenzene should be prepared from benzene. The sequence must include the diazonium salt at some stage. No mechanisms required.
  2. Write an equation showing the formation of ethanolamine from ethylene oxide. Show the mechanism by pushing electrons.
  3. Draw the structure of the carcinogenic nitrosamine formed when nitrous acid reacts with a 2° amine.


  1. Draw the structure of the product of benzenesulfonyl chloride plus

a)cyclopentylamine

b)dicyclopentylamine

  1. Draw and label a micelle of an anionic surfactant
  2. Write the formula and name of

a)a bar soap

b)a liquid soap

  1. Write the formula of a cationic surfactant
  2. Explain why amides are non basic (pKb  17). Draw a structure and push electrons.
    The lone pair of electrons on N is withdrawn to the carbonyl carbon by the electronegative O
  3. List the reagents required to convert an amide to:

a)a carboxylic acidH3O+, 

b)an carboxylic acid saltNaOH, H2O, 

  1. In the following list, circle amines that are more basic than aniline and draw a box around the ones that are less basic than aniline.
    Electron withdrawing groups reduce the basicity of amines. Electron donating groups increase the basicity of amines

  1. Explain why aniline cannot undergo Friedel Crafts reactions
    The amino group is a Lewis base. It reacts (donates its lone pair of electrons) to AlCl3, which is a strong Lewis acid. The resulting complex is not nucleophilic.
  2. Write equations for and show the mechanism of formation of p-aminoazobenzene from aniline and benzenediazonium sulfate
  3. Explain what an emulsion is and give an example of one.
    An emulsion is a stable mixture of 2 or more immiscible liquids held in suspension by a small percentage of emulsifier.
    e.g., o/w = oil in water emulsion such as milk. Water is the continuous phase and butterfat is the disperse phase
    e.g., w/o = water in oil emulsion such as butter. Water is the disperse phase and butterfat is the continuous phase.

  1. List 7 applications of cationic surfactants

a)they inhibit bacterial growth

b)they function as antistatic agents

c)they separate ores in floatation processes

d)they are corrosion inhibitors

e)used in hair conditioners

f)used in fabric softeners

g)their polymers are flocculants used to speed sedimentation

  1. Write chemical equations showing the conversion of a fatty acid to a quat.

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