Amines

Question 1

What impacts amines’ boiling point?

Answer 1

hydrogen bonding; directly related

more hydrogens, higher boiling point

Question 2

what impacts amines basicity?

Answer 2

resonance
aromaticity
hybridization (sp3 more basic than sp2 more basic than sp)

Question 3

what does high pka equal: strong base or weak base?

Answer 3

strong base

Question 4

What is an aryl amine?

Answer 4

Amine derived from an aromatic ring

Question 5

What is an akyl?

Answer 5

Structure with missing/replaced H

Question 6

What is an ammonium ion?

Answer 6

general name for positively charged or protonated substituted amines

Exp. HNR3+ and NH4+ (Has the + bc the N has 4 bonds/4 e- around it instead of 3 bonds and a lone pair)

Question 7

Do substituents increase the basicity of aryl (aromatic) amines, or decrease it?

Answer 7

It depends on the substituent

Electron withdrawing decreased basicity

Electron donating iNCREASES basicity

Question 8

Why are aryl (aromatic) amines generally LESS basic than alkyl (alkane) amines?

Answer 8

The resonance stabilization of the lone pair is lost/destroyed when the structure takes an H/gets protonated?

Question 9

What is another name for ammonium ion?

Answer 9

Ammonium salt

Question 10

what does polyalkylation do to a nitrogen?

Answer 10

It replaces the N’s hydrogens one by one until they’ve all been replaced (with Rs)

Question 11

At what ratio of carbons to nitrogens do amines become water soluable?

Answer 11

5:1 or less

If ratio is more than 5:1, aminie will be INsoluable

Question 12

how can you remember how electron donors and withdrawers impact an amine’s basicity?

Answer 12

donors donate basicity

withdrawers withdraw basicity

Question 13

what are the 5 newish ways you can make a PRIMARY amine?

Answer 13

1. Gabriel synthesis
2. Azide synthesis
3. Reduction of COOH derivative: nitrile
4. Reduction of COOH derivative: amide
5. Reduction of COOH derivative: aromatic substitution

Question 14

what are the 3 old ways you can make a PRIMARY amine?

Answer 14

1. SN2 polyalkylation
2. reduction of COOH
3. Redution of nitrobenzene

Question 15

what 2 reagents do you need for a reductive animation rxn?

Answer 15

a carbonyl, an amine, and [H+],NaBH3CN

Question 16

how might a reductive animation generate a product where the N ends up inside its own ring?

Answer 16

the N and the carbonyl were on the same ring to begin with

Question 17

when you’re trying to find the starting materials for a reduction animation product, what should you always do first?

Answer 17

Identify AAAAAALL of the C-N bonds

Question 18

what does a Hoffman elimiation basically do (to a molecule with an amine group on it)?

Answer 18

turns the amine group is to a leaving group, triggering it to leave and to leave a (LEAST SUBSTITUTED) alkene in its wake

Question 19

what are the reactants in a Hoffman elimination?

Answer 19

1. CH3I

2. Ag2O, H2O, heat