OCHEM LAB Exp9 (Amines and Amides)

amines and amides are organic compounds that contain ____

• nitrogen

Amines behave as ____ and are derivatives of _____

• organic base

• ammonia

Amides have a carbonyl group connected to a nitrogen atom [ H2C=N ] and are ____

• neutral

If hydrogens of ammonia [ NH3 ] are replaced by alkyl or aryl groups, it would result in formation of?

Amines

Smell of ____ resembles that of ammonia but not as sharp

Amines

Raw fish contains low MW amines such as?

• dimethylamine

• trimethylamine

Decaying flesh are suggestive of these compounds:

• putrescine

• cadaverine

↓ MW of Amine has what effect in its SOLUBILITY in water?

↓ MW of amine = ↑ solubility in water

How many carbons attached to nitrogen can be SOLUBLE in water?

4 or less

All amines are soluble in organic solvents like ____ or ____

• diethyl ether

• dichloromethane

Aliphatic/Chain Amines are (more or less) basic than ammonia?

More Basic

• chain amines are stronger base than ammonia

Aromatic/Ring Amines are (more or less) basic than ammonia?

Less basic

• ring amines are weaker base than ammonia

Amines + Acid → _____

Ammonia Salt (water-soluble)

Amides are _____ derivatives

carboxylic acid

Hydrolysis of amides can take place in either ____ or _____

acid or base

_____ are toxic chemicals; avoid excessive inhalation of its vapors; use gloves to avoid direct skin contact

Amines

_____ are more toxic than aliphatic amines and is READILY absorbed by the skin

Anilines

______ is extremely flammable

Diethyl ether

triethylamine + conc HCl forms what?

- White Fumes

- White Solid of triethylammonium chloride salt

Which amines were slightly soluble to H2O?

Aniline

N,N-Dimethylaniline

Odor of:

1. NH3

2. Triethylamine

3. Aniline

4. N,N-Dimethylaniline

5. Acetamide

1. NH3 = strong pungent

2. triethylamine = fishy

3. aniline = slightly fishy

4. NN-dimethylaniline = mild odor

5. Acetamide = mild to no odor

To test for Hydrolysis of Acetamide, what was added to it before boiling for 5mins?

Sulfuric Acid or H2SO4

Mosquito repellents contain DEET or ____?

N,N-diethyl-3-methylbenzamide

to make DEET, what carboxylic acid and amine do we use?

- m-toluic acid

- diethylamine

Metadone is a ____ ad dispensed as hydrochloride salt.

narcotic analgesic

Why is metadone dispensed as a hydrochloide salt?

1. salt is water soluble

2. more stable and longer shelf life

3. salt is less volatile

4. helps ensure accurate dosing and controlled release

Nicotine acts as a base or an alkaloid. What makes it react as a base?

Lone pair of Pyrrolidine (a pentagon with one N atom in the ring)

What happen in the hydrolysis of acetamide in ACIDIC MEDIUM?

CH3CONH2 + H2O + H+ ->

CH3COOH (acetic acid)

NH4 (ammonium ion)

What happens in hydrolysis of acetamide in BASIC MEDIUM?

CH3CONH2 + OH ->

CH3COO (acetate ion)

NH3 (ammonia gas)