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27 Cards in this Set

  • Front
  • Back
What is a nitrogen atom attached to four alkyl groups called?
Quarternary Ammonium Compound
Since the nitrogen carries a positive charge, amines usually exists as
In the common system, amines are generally named as alkylamines but in the IUPAC system the suffix _______ and prefix __________ are used.
suffix- amine
prefix- amino (used for naming compounds containing OH or CO2H groups)
What is the IUPAC name for amines that are derivatives of aniline?
What are carbamates?
Compounds with the general formula RNHC(O)OR'
What are carbamates also known as?
urethanes (which can form polymers called polyurethanes)
What are carbamates derived from?
Isocyanates (RNCO) + ROH
What is an enamine?
Nitrogen analog of an enol with amine group attached to one end fo double bond C=C-N
What is an imine?
Molecule with C=N double bond
What are nitriles?
Compounds with carbon-nitrogen triple bond.
What are nitriles also known as?
Nitriles are named with the prefix _________, and the suffix __________.
Prefix- Cyano
Suffix- nitrile
What are diazo compounds?
They contain a N2 functionality. Ex. C=N=N
What are azide compounds?
They contain N3 functionality.
Ex. N=N=N
Why do 3' amines have lower boiling points than 1' or 2'?
Because they can not form hydrogen bonds.
Why are aromatic amines less basic than aliphatic amines?
B/c the electron withdrawing effect of the ring reduces the basicity of the amino group.
What is the Gabriel synthesis?
Converts a 1'alkyl halide to 1' amine.
The Gabriel synthesis occurs via SN1/SN2 E1/E2.
How are nitro compounds reduced to 1' amines?
The most common reducing agent is Fe or Zn in dilute HCL and they reduce NO2 - NH2
How are nitriles reduced to 1' amines?
They are reduced with hydrogen and a catalyst or LAH.
Explain reductive amination.
A process where an aldehyde or ketone reacts with NH3 to produce and imine which is then reduced to an amine.
How are amides reduced to amines?
via LAH
Explain the Hoffman elimination.
Amine is converted to quarternary ammonium iodide via excess MEI then treated with Ag2O/H2O to an ammonium hydroxide which is then heated to produce an alkene + trisubstituted amine.
The reaction of benzamide with LiAlH4 yields...
a. benzoic acid
b. benzonitrile
c. benzylamine
d. ammonium benzoate
c. LiAlH4 is a strong reducer and reduces amides to amines.
Which of the following has the highest boiling point?
a. CH3NH2
b. CH3(CH2)6NH2
c. CH3(CH2)NH2
d. (CH3)3NH2
Molecular wt increases b.p. B has the highest molecular weight and therefore has the highest boiling point.
If 2-amino-3-methylbutane were treated with excess methyl iodide, silver oxide, and water what would be the major rxn products?
a. ammonia and 2-methyl-2-butene
b. trimethylamine and 3-methyl-1-butene
c. trimethylamine and 2-methyl-2-butene
d. ammonia and 2-methyl-1-butene
B. This is exhaustive methylation or Hoffman elimination. The products are a trisubstituted amine and an alkene. The leaset substituted alkene is the product.
What is the predominant alkene product in a Hoffman Elimination?
The least substituted alkene.