Chemistry: Amines

Anatomy and Physiology50 CardsCreated about 2 months ago

This flashcard set introduces the basic concept of amines, their classification into primary, secondary, and tertiary types, and outlines the preparation of aromatic amines from nitrobenzenes. It includes key reagents, reaction conditions, the chemical equation, and identifies the reaction type as reduction.

what are amines

compounds based on ammonia where one or more of the hydrogen atoms have been replaced by alkyl or aryl groups

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Key Terms

Term
Definition

what are amines

compounds based on ammonia where one or more of the hydrogen atoms have been replaced by alkyl or aryl groups

what can amines be classified as

primary secondary or tertiary

Preparation of aromatic amines from nitrobenzenes: reagents and conditions

Conc hcl and tin catalyst

Preparation of aromatic amines from nitrobenzenes: equation

Benzene-NO2 + 6[H] > benzene-NH2 + 2H2O

Preparation of aromatic amines from nitrobenzenes: reaction type

Reduction

Preparation of aromatic amines from nitrobenzenes: uses of aromatic amines

Dyes and drugs

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TermDefinition

what are amines

compounds based on ammonia where one or more of the hydrogen atoms have been replaced by alkyl or aryl groups

what can amines be classified as

primary secondary or tertiary

Preparation of aromatic amines from nitrobenzenes: reagents and conditions

Conc hcl and tin catalyst

Preparation of aromatic amines from nitrobenzenes: equation

Benzene-NO2 + 6[H] > benzene-NH2 + 2H2O

Preparation of aromatic amines from nitrobenzenes: reaction type

Reduction

Preparation of aromatic amines from nitrobenzenes: uses of aromatic amines

Dyes and drugs

General formula aliphatic amines

CnH2n+3N

Preparation of primary aliphatic amines from halogenoalkanes: reagents and conditions

Excess ammonia in ethanol and warm

Preparation of primary aliphatic amines from halogenoalkanes: general equation

RBr + 2NH3 > RNH2 + NH4+Br-

Preparation of primary aliphatic amines from halogenoalkanes: mechanism

Nucleophilic substitution

Preparation of primary aliphatic amines from halogenoalkanes: why must excess ammonia be used

To prevent further substitution

Preparation of primary aliphatic amines from nitriles: reagents and conditions

H2 Ni catalyst

Preparation of primary aliphatic amines from nitriles: general equation

R-C(triple bond)N + 2H2 > RCH2NH2

Base

Substance that accepts H+ ions

Why are ammonia and amines weak bases

Lone pair of electrons on the nitrogen atom, which can accept a proton from an acid

What do amines dissolve in acids to give

The corresponding alkyl-ammonium salt

How can the amine be reformed from an alkylammonium salt

By adding an alkali

What is the ability of a substance to act as a base termed

Basicity

What is the order of basicity of amines

Primary amines>NH3>benzene NH2

Comparing primary aliphatic amines and ammonia: what does the alkyl group in primary amines release and why

Electron density towards the nitrogen atom due to positive inductive effect

Comparing primary aliphatic amines and ammonia: what does release of electron density towards nitrogen atom increase

Electron density on the nitrogen atom and the lone pair is more available to accept H+


Comparing primary aliphatic amines and ammonia: are aliphatic amines stronger bases than ammonia

Yes

Comparing primary aromatic amines and ammonia: where is the lone pair of electrons on the nitrogen atom of aromatic amines

Delocalised into the pi ring

Comparing primary aromatic amines and ammonia: what effect does the delocalisation of the lone pair have on the electron density of the nitrogen atom

Decreases it- lone pair less available to accept H+

Comparing primary aromatic amines and ammonia: are aromatic amines weaker bases than ammonia

Yes

What does relative basicity depend on

The availability of the lone pair on the N atom

The more available the lone pair is, the ? The base

Stronger

Why are amines nucleopgiles

Nitrogen atom of amines able to donate a lone pair of electrons

Nucleopgile

Electron pair donor

Reaction of ammonia with halogenoalkanes: general equation

R-Hal + 2NlpH3 > RNlpH2+ NH4+Hal-

Reaction of ammonia with halogenoalkanes: mechanism

Nuc substitution

Reaction of primary amines with halogenoalkanes: general equation

RHal + 2R1NlpH2 > RR1NH + R1NH3+Hal-

Reaction of secondary amines with halogenoalkanes: general equation

RHal + 2R1(sq)NH > RR1(sq)N + R1(sq)NH2+Hal-

Reaction of tertiary amines with halogenoalkanes: general equation

R-Hal + R1(cub)N > RR1(cub)N+Hal-

What are quaternary ammonium salts used as

Cationic surfactants in household products such as detergent and fabric softeners

What are surfactants

Compounds with regions which are partly soluble in water and partly insoluble

What charge do quaternary ammonium salts have

Positive- cationic

Which region of the quaternary ammonium salt is ionic

The N+

| Soluble in water

Which part of the quaternary ammonium salt is not water soluble

The long non polar hydrocarbon region

Nucleophilic addition elimination reactions of ammonia with acyl chlorides: general equation

RCOCl + NH3 > RCONH2 + H+ + Cl-

Nucleophilic addition elimination reactions of ammonia with acyl chlorides: organic product

Amide

Nucleophilic addition elimination reactions of ammonia with acyl chlorides: mechanism

Nuc addition elimination

Nucleophilic addition elimination reactions of amines with acyl chlorides: general equation

RCOCl + R1NH2 > RCONHR1 + H+Cl-

Nucleophilic addition elimination reactions of amines with acyl chlorides: organic product

N substituted amide

Nucleophilic addition elimination reactions of ammonia with acid anhydrides: general equation

RCOOCOR + NH3 > RCONH2 + RCOOH

Nucleophilic addition elimination reactions of ammonia with acid anhydrides: organic product

Amide and carboxylic acid

Nucleophilic addition elimination reactions of amines with acid anhydrides:

RCOOCOR + R1NH2 > RCONR1H + RCOOH

Nucleophilic addition elimination reactions of amines with acid anhydrides: organic product

N substituted amide

equation for ethyl amine and acid (HCl)

CH3CH2NH2 + HCl > CH3CH2N+H3Cl-

equation for alkylammonium salt and alkali

CH3CH2NH3 + OH- > CH3CH2NH2 + H2O