Organic Chemistry

Functional groups

24.4

Functional Group Chemistry

Alcohols contain the hydroxyl functional group and have the general formula R-OH.

Sterols, ethylene glycol

C6H12O6 (aq) 2CH3CH2OH (aq) + 2CO2 (g)enzyme

CH2 CH2 (g) + H2O (g) CH3CH2OH (g)H2SO4

Biological production of ethanol

Commercial production of ethanol

DRINKABLE vs. DENATURED Alcohol

24.4

Functional Group Chemistry

Ethers have the general formula R-O-R’.

CH3OH + HOCH3 CH3OCH3 + H2OH2SO4

catalyst

Condensation Reaction

24.4

Functional Group Chemistry

Aldehydes and ketones contain the carbonyl ( ) functional group.

O

C

R C H

O

• aldehydes have the general formula

R C R’

O

• ketones have the general formula

H C H

O

H C

O

CH3 C

O

CH3H3C

formaldehyde acetaldehyde acetone

24.4

Functional Group Chemistry

Carboxylic acids contain the carboxyl ( -COOH ) functional group.

VINEGAR, ASPIRIN , ANTS, CITRUS FRUITS, PROTEINS, PRESERVATIVES

24.4

Functional Group Chemistry

Esters have the general formula R’COOR, where R is a hydrocarbon group.

CH3COOH + HOCH2CH3 CH3 C O CH2CH3 + H2O

O

ethyl acetate

Banana: isopentyl acetatePineapple: ethyl butanoateApple: methyl butanoatePear: propyl ethanoateOrange: Octyl ethanoateRaspberry: 2-Methylpropyl ethanoateOil of Wintergreen: methyl salycilate

HOW TO MIMIC NATURE: Making synthetic flavoring

• A good cherry is supposed to be tough to formulate.  Here is an example of a *minimum* synthetic cherry flavoring:

•         ethyl methyl p-tolyl glycidate          16.0 %         iso-amyl acetate                        12.0 %         iso-butyl acetate                       12.0 %         p-methyl benzyl acetate                 11.0 %         benzaldehyde                             8.0 %         vanillin                                 7.0 %         benzyl alkcohol                          5.5 %         piperonal                                5.0 %         ethyl caprate                            4.0 %         cinnamic aldehyde dimethyl acetal        3.0 %         p-tolyl aldehyde                         3.0 %         cinnamyl anthranilate                    3.0 %         ethyl caproate                           2.0 %         geranyl butyrate                         2.0 %         terpenyl butyrate                        0.5 %

Functional Group Chemistry

Amines are organic bases with the general formula R3N.

CH3NH2 + H2O RNH3+ + OH-

Urea

Phenylpropanolamine

(Meth)amphetamine

Caffeine

24.4

Blue jeans

• Indigo: an ancient dye, herbal remedy, poison

• Indigofera

• Tyrian purple – 6,6’-dibromoindigo

The sweet life

saccharinaspartame

sucralose

Drugs

aspirin

cocaine

POLYMERS• Poly: Many Meros: Parts• Made up of repeating monomers

• Copolymer is a polymer made up of two or more monomers

• Common biopolymers: Proteins, DNA, RNA, starch, cellulose

( CH CH2 CH2 CH CH CH2 )n

• PET: Polyethylene terephthalate– Plastic bottles

• Polytetrafluoroethylene– Teflon™

• Polypropylene• Polystyrene• Polyvinyl chloride• Nylon (synthetic

polyamide, similar to bonds in proteins)

http://www.nationalgeographic.com/education/plastics/index.html

The stuff of life

• DNA

The stuff of life

• Proteins