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27 Cards in this Set
- Front
- Back
What is a nitrogen atom attached to four alkyl groups called?
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Quarternary Ammonium Compound
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Since the nitrogen carries a positive charge, amines usually exists as
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salts
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In the common system, amines are generally named as alkylamines but in the IUPAC system the suffix _______ and prefix __________ are used.
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suffix- amine
prefix- amino (used for naming compounds containing OH or CO2H groups) |
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What is the IUPAC name for amines that are derivatives of aniline?
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Benzenamine
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What are carbamates?
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Compounds with the general formula RNHC(O)OR'
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What are carbamates also known as?
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urethanes (which can form polymers called polyurethanes)
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What are carbamates derived from?
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Isocyanates (RNCO) + ROH
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What is an enamine?
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Nitrogen analog of an enol with amine group attached to one end fo double bond C=C-N
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What is an imine?
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Molecule with C=N double bond
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What are nitriles?
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Compounds with carbon-nitrogen triple bond.
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What are nitriles also known as?
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Cyanides
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Nitriles are named with the prefix _________, and the suffix __________.
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Prefix- Cyano
Suffix- nitrile |
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What are diazo compounds?
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They contain a N2 functionality. Ex. C=N=N
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What are azide compounds?
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They contain N3 functionality.
Ex. N=N=N |
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Why do 3' amines have lower boiling points than 1' or 2'?
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Because they can not form hydrogen bonds.
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Why are aromatic amines less basic than aliphatic amines?
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B/c the electron withdrawing effect of the ring reduces the basicity of the amino group.
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What is the Gabriel synthesis?
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Converts a 1'alkyl halide to 1' amine.
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The Gabriel synthesis occurs via SN1/SN2 E1/E2.
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SN2
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How are nitro compounds reduced to 1' amines?
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The most common reducing agent is Fe or Zn in dilute HCL and they reduce NO2 - NH2
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How are nitriles reduced to 1' amines?
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They are reduced with hydrogen and a catalyst or LAH.
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Explain reductive amination.
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A process where an aldehyde or ketone reacts with NH3 to produce and imine which is then reduced to an amine.
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How are amides reduced to amines?
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via LAH
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Explain the Hoffman elimination.
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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.
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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.
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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.
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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.
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What is the predominant alkene product in a Hoffman Elimination?
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The least substituted alkene.
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