Organic Nitrogen Compounds

Question 1

Electronegative N causes?

Answer 1

Dipole moment ^_^

Question 2

Amine properties

Answer 2

• Higher melting and boiling points than equivalent alkanes
• If <6 Cs soluble in water
• Weak bases due to lone pair on N

Question 3

Aliphatic amines

Answer 3

Chained amines

Question 4

Aliphatic vs aromatic amine bases

Answer 4

Aliphatic=stronger bases

Question 5

Aromatic amine preparation

Answer 5

reduce a nitroarene

Question 6

Aliphatic amine preparation

Answer 6

Reduce a nitrile

Question 7

Amines and halogenoalkanes

Answer 7

Amines=nucleophiles and nucleophilic substitution occurs

Question 8

Amide features

Answer 8

Can be primary, secondary or tertiary

Primary amide formula: RCONH2

Have C=O double bond

Stable compounds

Question 9

Primary amide synthesis

Answer 9

Created via NH3 and acyl chloride/acid anhydride resction

CH3COCl+NH3 →CH3CONH2+HCl
NH3+HCl→NH4Cl

Question 10

Secondary amide synthesis

Answer 10

CH3COCl + CH3NH2 →CH3CONHCH3 + HCl

Question 11

Amides from carboxylic acids

Answer 11

Convert carboxylic acid into acyl chloride

Question 12

Acid hydrolysis of amide

CH3CONH2 + H2O + HCl

Answer 12

→carboxylic acid + ammonium salt

CH3COOH + NH4+Cl-

Question 13

Alkaline hydrolysis of amide

CH3CONH2 + NaOH

Answer 13

→acid salt and ammonia

CH3COO-Na+ + NH3

Question 14

Amide dehydration by phosphorus pentoxide

Answer 14

Form nitriles

Question 15

Amines + acids

Answer 15

Form ionic salts

Question 16

Amino acids

Answer 16

Amine + carboxylic acid

Reaction = salts with both acids and bases

Question 17

Nitriles

Answer 17

RCN

Reduced to amines via LiAlH4 in ether

Hydrolysed to carboxylic acids by boiling aqueous acids

Question 18

Amides

Answer 18

RCONH₂

Weaker than amines

Made via ammonium salt dehydration

Reduced to amines via LiAlH₄

Dehydrated to nitriles via P2O5

Question 19

Hofmann degredation

Answer 19

Amides to amines via Br₂ + NaOH

Reduces C skeleton by 1