Chapter 14 repeat

Hydrolysis of fat (saponification)

Micelle formation (soap action)

Detergents

Condensation polymers

PETEPEN

Condensation Polymers• Polyesters are condensation polymers• They are formed by eliminating a small

molecule (e.g., H2O) when combining: – Diacid– Diol

• Each of the combining molecules has two reactive functional groups, highlighted in red

14.2

Est

ers

Polethylene terphthalate, PETE

COOHHOOC + OH CH2CH2OHnH+

Terphthalic acid 1,2-ethanediol

CCO

O CH2CH2OO

* *n

Continued condensationat each end

Repeating unit of the polymer

CHOOCO

O CH2CH2OH+ H2OPETE is used in:

•Mylar•Plastic bottles•Polyester fabric

PEN

O

OH

O

HO

Polymers

14.4 Nature’s High Energy Compounds: Phosphoesters and Thioesters

• Phosphoric acid reacts with alcohols to produce a phosphate ester or phosphoester

• The ester can then react with a second or third acid to give phosphoric acid anhydrides

• ADP and ATP of biochemistry fame are important examples of phosphate esters

15

adenosinetriphosphate, ATP

P

O

O

O O P

O

O

O

N

OHOH

OO CH2

N

NN

NH2

P

O

O

Phosphoric Acid Esters

Ester bond

Anhydride bonds

14.4

Nat

ure’

s H

igh

Ener

gy C

ompo

unds

:

Phos

phoe

ster

s an

d Th

ioes

ters

Phosphate esters

Thioesters

• In biochemistry, acetyl coenzyme A (acetyl CoA-SH) reacts with acyl groups to “activate” them for further biological reaction by forming a thioester

CH3CO

CoA-SCOO

-

CCH2COO

-

O+ CCH2

COO-

COO-

CH2COO

-

OH

+CoA-SH

Acetyl CoA

14.4

Nat

ure’

s H

igh

Ener

gy C

ompo

unds

:

Phos

phoe

ster

s an

d Th

ioes

ters

Pheromones

O

O

(E)-tetradec-11-enyl acetate

Pain killersO

OH

Ibuprofen

O

NH

OH

Acetaminophen

O

HO

O

Naproxen

(paracetamol)

Painkillers and pheromones

Structures of Four Prostaglandins17

.2 F

atty

Acid

s

Prostaglandin synthesis

Prostaglandins