Amines

Question 1

Amine Outline

Answer 1

Organic relatives of ammonia (NH3). At least 1 H is replaced by an organic (C based) substituent, includes a lone pair. Tetrahedral geometry. Contains amide (C to N) bonds

Question 2

Primary Amine

Answer 2

2 H and 1 organic substituent attached to N

Question 3

Secondary amine

Answer 3

1 H and 2 organic substituents attached to N

Question 4

Tertiary amine

Answer 4

0 H and 3 organic substituents attached to N

Question 5

Relationship between substituents, H bonds and boiling points

Answer 5

More H substituents = more H bonds = higher boiling point. Primary amines have a higher boiling point then secondary that themselves have a higher boiling point then tertiary

Question 6

Amine Characteristics

Answer 6

Dictated by lone pairs. Both basic (lone pair attracts Hs) and nucleophilic (lone pair can be donated to electrophilic molecules)

Question 7

Basic Reactions

Answer 7

amine + acid -> amine salt (N = positive =salt)

Question 8

Alkyl Halide Reactions

Answer 8

Amine + alkyl halide -> ammonium salt + anion (halogen)

Question 9

Aldehyde/Ketone and Amines Reactions

Answer 9

Aldehyde/ketone + amine -> Imine

Question 10

Carboxylic Acid and Amines Derivatives

Answer 10

carboxylic acid + amine -> amide

Question 11

Amine Basicity (least to most)

Answer 11

aniline (N-R1-R2-benzene ring), ammonia, cyclohexylamine (N-R1-R2-non aromatic ring) and methylamine (N-CH3-R1-R2)

Question 12

Relationship between substituents and basicity

Answer 12

Electron donating group = higher electron density N = N more nucleophilic = more reactive = more alkaline. The more complex the substituents = the harder electrophiles to attach. Primary amine = more reactive

Question 13

Amine Alkylation Outline

Answer 13

Sn2 Reaction. amine/amide + alkyl halide -> amine salt

Question 14

Conversion of an amine salt to amine (theoretically)

Answer 14

amine salt + NaOH -> amine

Question 15

Why can’t a salt really be converted to a primary amine

Answer 15

Primary amine is very reactive (very alkaline), so replaces reactant (ammonia)

Question 16

Imine Outline

Answer 16

Intermediate of amino acid biosynthesis. Can be reduced back to amines

Question 17

Amino Acid Outline

Answer 17

Amine group and carboxylic acid group. 9 essential amino acids and 11 non-essential amino acids

Question 18

Amine Drugs Outline

Answer 18

Lipophilic, low solublility in plasma. Aministered as hydrochloride salts to increase solubility (lets chains >5 Cs more soluble)