CHAPTER 13

CONCURRENT ENROLLMENT

ALCOHOLAlcohol– A compound in which an -OH group is

connected to an aliphatic carbon atomCH3-CH2-OH ethanolOverheadCholesterol ends in -ol, so there must be a -OH attached to a large carbon chainHydroxy group (-OH) replaces a -HPhenol– A compound in which an -OH group is

connected to a benzene ring. The parent compound is also called phenol

Considered to have derived from water H-OH, the hydrogen is replace by an R group or a benzene ring

ETHER AND NOMENCLATUREEther – A compound that contains a -CH2-O-CH2-– Overhead

Carbon R groups replace both hydrogen's in a water H-O-H ---> R-O-R’ etherIUPAC rules for naming alcoholsName the longest chain in which the hydroxy group is attached. Change the ending to -olNumber the longest chain so that the hydroxy group has the lowest numberLocate and name any other groups attached to the chainLearning check page 416Learning check page 417

CLASSIFICATIONPrimary alcohols– An alcohol in which the -OH group is attached

to CH3- or to a carbon attached to one other carbon atom

Secondary alcohols– An alcohol in which the carbon bearing the -OH

group is attached to two other carbon atoms

Tertiary alcohols– An alcohol in which the carbon bearing the -OH

group is attached to three other carbon atoms

Table 13.1 on page 418Learning check page 418Overhead

PHYSICAL PROPERTIESThe lower molecular weight alcohols are completely miscible with water (mixes)As the chain increases the properties become less water-like and more alkane-like. Less soluble in water and more soluble in nonpolar solventsLearning check page 418Reactions of alcoholsDehydration - water is chemically removed from a compoundElimination reactions– A reaction in which two or more covalent bonds are broken

and a new multiple bond is formedHow reactions occur page 421

DEHYDRATION TO PRODUCE AN ETHER

Overhead R-O-H + H-O-R ------------------------> R-O-R + H2O Alcohol alcohol H2SO4, 140oC EtherOxidation– An oxidation reaction occurs when one molecule gains an oxygen

atom and the other molecule loses hydrogen’s– An oxidation agent (like potassium dichromate or potassium

permanganate) will be represented by a (O)Each alcohol reacts differently with oxidizing agentsPrimary alcohols

CONTINUE

Tertiary alcohols do not react with oxidizing agents

MULTISTEPPVC Formed from a multistep ethene forming vinyl chloride to PVCEthene to diethyl etherCH2=CH2 + H2O --------> CH3CH2-OH H2SO4 2CH3CH2-OH -----------> CH3CH2-O-CH2CH3 + H2O H2SO4, 140oCStudy skills page 425Fermentation– A reaction of sugars, starch, or cellulose to

produce ethanol and carbon dioxideMost ethanol used in industry is produced from ethylene and water

CONTINUERead page 427-431Antioxidant– A substance that prevents another substance

form being oxidized– Phenols can do this

Learning check page 432 13.15Alkoxy group the -O-R functional group. Change the -yl of a side change to -oxy-O-CH3 methoxy-Learning check 13.16Heterocyclic ring– A ring in which one or more atoms are an atom

other than carbon

PROPERTIES OF ETHERSEthers are slightly more soluble in water than hydrocarbons but less soluble than alcoholsNo hydrogen bonds are formed with other ether molecules in pure state so it has low boiling pointsInert do not react with most reagentsFlammableEthyl ether was the first general anesthetic

THIOLSA compound containing an -SH groupSulfhydryl is a -SH functional groupDisulfide– A compound containing an -S-S- group

2R-SH + (O) ---> R-S-S-R + H2OPage 434 picturesMetal ions (M2+) react with sufhydryl groups2R-SH + M2+ ---> R-S-M-S-R + 2H+

Learning checks page 435

POLYFUNCTIONAL COMPOUNDS

A compound with two or more functional groupsCholesterol– Has two functional groups alkenes and

alcoholsActive ingredient in marijuana, tetrahydrocannabinolHas three functional groups, alkene, ether, and phenolPage 436