13: Amines (Part 1) Flashcards
this uses an aldehyde or ketone to replace one H atom on a nitrogen atom by an alkyl group, making a more substituted amine
reductive amination
____________ and ___________ amines are also capable of intermolecular hydrogen bonding, because they contain N – H bonds.
Primary, secondary
_______________ groups add electron density to the benzene ring, making the arylamine
more basic than aniline
Electron-donor
Nucleophilic attack of NH3 on the carbonyl group forms an?
imine
All amines having _________ are H2O soluble because they can hydrogen bond with H2O.
≤ 5 C’s
these are classified as 1°, 2°, or 3° by the number of alkyl groups bonded to the nitrogen atom
amines
Amines are ___________ in organic solvents regardless of size
soluble
this replaces a C=O by a C – H and C – N bond
reductive amination
Reduction of the imine forms an?
amine
The Gabriel synthesis begins with reaction of primary alkyl halide with phthalimide, followed by?
hydrolysis
these react as nucleophiles with compounds that contain electrophilic carbons
amines
these are more basic than NH3
alkylamines
The ______________________ converts an alkyl halide into a 1° amine by a two-step process
Gabriel synthesis
these react as bases with a variety of organic and inorganic acids
amines
Three types of reactions are used to prepare an amine:
[1] Nucleophilic substitution using nitrogen nucleophiles
[2] Reduction of other nitrogen-containing functional groups
[3] Reductive amination of aldehydes and ketones
Electron-withdrawing groups remove electron density from the benzene ring, making the arylamine _________ than aniline
less basic
these are stronger bases and nucleophiles than other neutral organic compounds
amines
Amines exhibit ______________ interactions because of the polar C – N and N – H bonds.
dipole–dipole
Amines having _________ are H2O insoluble because the nonpolar alkyl portion is too large to dissolve in the polar H2O solvent
> 5 C’s
Any factor that decreases the electron density (electron withdrawing groups) on N decreases an amine’s?
basicity
these are less basic than alkylamines
arylamines
The Gabriel synthesis converts an alkyl halide into a 1° amine by a two-step process:
nucleophilic substitution followed by hydrolysis
this adds one R group to the nitrogen atom
reductive amination
Any factor that decreases the electron density (______________________________) on N decreases an amine’s basicity
electron withdrawing groups
these are organic nitrogen compounds
amines
In terms of increasing basicity:
amides < arylamines < NH3 < 1o < 2o < 3o
this is formed by replacing one or more hydrogen atoms of ammonia (NH3) with alkyl groups
amines
Substituted anilines are more or less basic than ___________ depending on the nature of the substituent
aniline
these react as bases with compounds that contain acidic protons
amines
final product in nucleophilic substitution of amines
quaternary ammonium salt
Electron-donor groups add electron density to the benzene ring, making the arylamine
_______________ than aniline.
more basic
Any factor that increases the electron density (__________________________) on the N atom increases an amine’s basicity
electron donating groups
The Gabriel synthesis begins with reaction of primary alkyl halide with ______________, followed by hydrolysis
phthalimide
Amides are much less ______ than amines
basic
this begins with reaction of primary alkyl halide with phthalimide, followed by hydrolysis
Gabriel synthesis
this exhibit dipole–dipole interactions because of the polar C – N and N – H bonds
Amines
The most effective reducing agent for reductive amination of aldehyde and ketone is?
sodium cyanoborohydride (NaBH3CN)
With a 1° or 2° amine as starting material, ______________________ is used to prepare 2° and 3° amines, respectively.
reductive amination
______________________ groups remove electron density from the benzene ring, making the arylamine less basic than aniline.
Electron-withdrawing
this is a two-step method that converts aldehydes and ketones into 1°, 2°, and 3° amines
reductive amination
