Chemistry of Amines

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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Synthesis of Amines

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