CHAPTER 13 CONCURRENT ENROLLMENT

ALCOHOL Alcohol –A–A–A–A compound in which an -OH group is connected to an aliphatic carbon atom CH3-CH2-OH ethanol Overhead Cholesterol ends in -ol, so there must be a -OH attached to a large carbon chain Hydroxy group (-OH) replaces a -H Phenol –A–A–A–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 NOMENCLATURE Ether –A–A–A–A compound that contains a -CH2-O-CH2- –O–O–O–Overhead Carbon R groups replace both hydrogen's in a water H-O-H ---> R-O-R’ ether IUPAC rules for naming alcohols Name the longest chain in which the hydroxy group is attached. Change the ending to -ol Number the longest chain so that the hydroxy group has the lowest number Locate and name any other groups attached to the chain Learning check page 416 Learning check page 417

CLASSIFICATION Primary alcohols –A–A–A–An alcohol in which the -OH group is attached to CH3- or to a carbon attached to one other carbon atom Secondary alcohols –A–A–A–An alcohol in which the carbon bearing the -OH group is attached to two other carbon atoms Tertiary alcohols –A–A–A–An alcohol in which the carbon bearing the -OH group is attached to three other carbon atoms Table 13.1 on page 418 Learning check page 418 Overhead

PHYSICAL PROPERTIES The 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 solvents Learning check page 418 Reactions of alcohols Dehydration - water is chemically removed from a compound Elimination reactions –A–A–A–A reaction in which two or more covalent bonds are broken and a new multiple bond is formed How reactions occur page 421

DEHYDRATION TO PRODUCE AN ETHER Overhead R-O-H + H-O-R > R-O-R + H2O Alcohol alcohol H2SO4, 140oC Ether Oxidation –A–A–A–An oxidation reaction occurs when one molecule gains an oxygen atom and the other molecule loses hydrogen’s –A–A–A–An oxidation agent (like potassium dichromate or potassium permanganate) will be represented by a (O) Each alcohol reacts differently with oxidizing agents Primary alcohols

CONTINUE

MULTISTEP PVC Formed from a multistep ethene forming vinyl chloride to PVC Ethene to diethyl ether CH2=CH2 + H2O > CH3CH2-OH H2SO4 2CH3CH2-OH > CH3CH2-O-CH2CH3 + H2O H2SO4, 140oC Study skills page 425 Fermentation –A–A–A–A reaction of sugars, starch, or cellulose to produce ethanol and carbon dioxide Most ethanol used in industry is produced from ethylene and water

CONTINUE Read page Antioxidant –A–A–A–A substance that prevents another substance form being oxidized –P–P–P–Phenols can do this Learning check page Alkoxy group the -O-R functional group. Change the -yl of a side change to -oxy -O-CH3 methoxy- Learning check Heterocyclic ring –A–A–A–A ring in which one or more atoms are an atom other than carbon

PROPERTIES OF ETHERS Ethers are slightly more soluble in water than hydrocarbons but less soluble than alcohols No hydrogen bonds are formed with other ether molecules in pure state so it has low boiling points Inert do not react with most reagents Flammable Ethyl ether was the first general anesthetic

THIOLS A compound containing an -SH group Sulfhydryl is a -SH functional group Disulfide –A–A–A–A compound containing an -S-S- group 2R-SH + (O) ---> R-S-S-R + H2O Page 434 pictures Metal ions (M2+) react with sufhydryl groups 2R-SH + M2+ ---> R-S-M-S-R + 2H+ Learning checks page 435

POLYFUNCTIONAL COMPOUNDS A compound with two or more functional groups Cholesterol –H–H–H–Has two functional groups alkenes and alcohols Active ingredient in marijuana, tetrahydrocannabinol Has three functional groups, alkene, ether, and phenol Page 436