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Section 23 - Amines

The Chemistry of Amines - Section 23 of Organic Chemistry Notes is 19 pages in length (page 23-1 through page 23-19) and covers ALL you'll need to know on the following lecture/book topics:

SECTION 23 - Amines

23-1 -- Primary (1°), Secondary (2°), and Tertiary (3°) Amines
23-1 -- Nomenclature of Amines

  · Common Names – “Alkyl Amines”
  · IUPAC Names – “Alkanamines”
  · Naming Amines With –NH2 as a Substituent (Branch)
  · Use of “N-“ as a Locator
  · Ammonium and Iminium Ions
23-3 -- Structures of Amines
  · Simple Amines are Pyramidal
  · Complicated Amines (i.e. Aniline) Can “Flatten Out”
23-4 -- Spectroscopy of Amines
  · IR Spectroscopy of Amines
  · 1H NMR Spectroscopy of Amines
23-5 -- Basicity of Amines
  · Amine Basicity Relative to H2O and OH-
  · Alkylamines and Their Conjugate Acids (pKa ~ 10-11)
  · Resonance Effects and Electron-Withdrawing Substituents
23-7 -- Acidity of Amines
  · Alkyl Amines (pKa ~ 35-38) Have Very Strong Conj. Bases - Amide Ions, R2N-
23-8 -- Reactions of Amines – pp.23-8 through pp.23-19 – BIG TOPIC
23-8 -- Alkylation of Amines

  · Direct Alkylation of Amines (SN2 with Amines as Nucleophiles)
  · Exhaustive Alkylation of Amines
  · Reductive Alkylation of Amines (Use of NaBH4 or H2/catalyst)
23-10 -- Gabriel Synthesis of 1° Amines
  · Use of Pthalimide in an SN2 Reaction
  · Gabriel Synthesis Adds –NH2 to the R-group of R-Br
23-12 -- Preparation of Amines via Reduction Reactions
  · Reduction of Azides (R-N3)
  · Reduction of Nitriles (R-CΞN:)
  · Reduction of Amides Using Lithium Aluminum Hydride (LiAlH4, or “LAH”)
23-13 -- The Hofmann Elimination
  · Step 1 - Overalkylation of the Amino Group
  · Step 2 – “Switching” I- with OH-
  · Step 3 - E2 Elimination (via Heat, Δ) to Form Less-Substituted Alkene
  · “Hofmann Regiochemistry” is Observed
23-14 -- The Hofmann Rearrangement
  · Involves Transformation of 1° Amide in Basic Solution to an Amine
23-15 -- The Curtius Rearrangement
  · Converts an Acyl Azide to an Amine
  · Mechanism Involves an Isocyanate Intermediate (O=C=N-R)
  · Curtius Rearrangements Performed in H2O vs. in Alcohol (R’OH)
23-16 -- Diazonium Ion Chemistry
  · [ R-NΞN <--> R-N=N ]+1 , an Alkyl Diazonium Ion (Add lone pairs on N’s!!)
  · N2 is an Excellent Leaving Group (l.g.)
  · Diazonium Ions are Very Unstable
  · Aryl Diazonium Ions (Ar-NΞN:)+1 are More Stable
  · Aryl Diazonium Ions in Electrophilic Aromatic Substitution (E.A.S) Reactions
  · Azobenzenes and UV-VIS Spectroscopy
23-18 -- Rearrangement of Alkyl Azides
  · Analogous to Curtius Rearrangement
  · Rearrangement Occurs Thermally (via Heat), or Photochemically (via UV light)

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