Alcohols An alcohol contains a hydroxyl group ( OH) attached to a carbon chain. A phenol contains a hydroxyl group ( OH) attached to a benzene ring.

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1 Chapter : rganic Compounds with xygen Alcohols, Ethers Alcohols An alcohol contains a hydroxyl group ( H) attached to a carbon chain. A phenol contains a hydroxyl group ( H) attached to a benzene ring. Naming Alcohols The names of alcohols in IUPAC replace the e with ol. with common names use the name of the alkyl group followed by alcohol. Formula IUPAC CH4 methane CH3 H methanol CH3 CH3 ethane CH3 CH2 H ethanol IUPAC names for longer chains number the chain from the end nearest the H group. CH3 CH2 CH2 H 1 propanol H CH3 CH CH2 CH3 2 butanol CH3 H CH3 CH CH2 CH2 CH CH3 5 methyl 2 hexanol Phenols in Medicine Derivatives of Phenol Compounds of phenol are the active ingredients in the essential oils of cloves, vanilla, nutmeg, and mint. Naming Phenols To name a phenol with two substituents, assign C 1 to the carbon attached to the H. number the ring to give the lowest numbers. Ethers An ether contains an between two carbon groups. has a common name that gives the alkyl names of the attached groups followed by ether. CH3 CH3 dimethyl ether CH3 CH2 CH3 ethyl methyl ether

2 Ethers as Anesthetics Anesthetics inhibit pain signals to the brain. like diethyl ether CH3 CH2 CH2 CH3 were used for over a century, but caused nausea and were flammable. developed by the 1960 s were nonflammable. Properties of Alcohols and Ethers, Boiling Points of Alcohols contain polar H groups. form hydrogen bonds with other alcohol molecules. have higher boiling points than alkanes and ethers of similar mass. Boiling Points of Ethers do not have a polar group. have an atom, but there is no H attached. cannot form hydrogen bonds between ether molecules. Solubility of Alcohols and Ethers in Water Alcohols and ethers are more soluble in water than alkanes because the oxygen atom can hydrogen bond with water. with 1 4 C atoms are soluble, but not with 5 or more C atoms. Comparing Solubility and Boiling Points Molar Boiling Soluble Compound Mass Point ( C) in Water? Alkane CH3 CH2 CH No Ether CH3 CH Yes Alcohol CH3 CH2 H Yes Solubility of Phenol is soluble in water. has a hydroxyl group that ionizes slightly (weak acid). is corrosive and irritating to skin. Reactions of Alcohols Combustion of Alcohols Alcohols undergo combustion with 2 to produce C2 and H2. 2CH3H C2 + 4H2 + Heat

3 Dehydration of Alcohols Alcohols undergo dehydration when heated with an acid catalyst. the loss of H and H from adjacent carbon atoms. H H H +, heat H C C H H C=C H + H2 H H H H alcohol alkene CH3 CH CH3 CH3 CH=CH2 + H2 xidation and Reduction In an oxidation, there is an increase in the number of C bonds. there is a loss of H. In a reduction, there is an decrease in the number of C bonds. there is a gain of H. xidation and Reduction xidation of Primary (1 ) Alcohols When a primary alcohol is oxidized, [], one H is removed from the H. another H is removed from the carbon bonded to the H. an aldehyde is produced. [] Primary alcohol > Aldehyde H [] CH3 C H CH3 C H + H2 H Ethanol Ethanal (ethyl alcohol) (acetaldehyde) xidation of Secondary (2 ) Alcohols When a secondary alcohol is oxidized, [], one H is removed from the H. another H is removed from the carbon bonded to the H. a ketone is produced.

4 [] secondary alcohol ketone H [] CH3 C CH3 CH3 C CH3 + H2 H 2 propanol (isopropyl alcohol) 2 propanol (dimethyl ketone) xidation of Tertiary ( 3) Alcohols Tertiary 3 alcohols do not readily oxidize. [] Tertiary alcohol no reaction H [] CH3 C CH3 no product CH3 no H on the C H to oxidize 2 methyl 2 propanol xidation of Ethanol in the Body In the body, enzymes in the liver oxidize ethanol. aldehyde product impairs coordination. blood alcohol over 0.4% can be fatal. CH3CH2H > CH3CH > CH3CH > 2C2 + H2 ethyl alcohol > acetaldehyde > acetic acid Ethanol CH3CH2H Ethanol acts as a depressant. kills or disables more people than any other drug. is metabolized at a rate of mg/dl per hour by a social drinker. is metabolized at a rate of 30 mg/dl per hour by an alcoholic.

5 Effect of Alcohol on the Body Alcohol Contents in Common Products % Ethanol Product 50% Whiskey, rum, brandy 40% Flavoring extracts 15 25% Listerine, Nyquil, Scope 12% Wine, Dristan, Cepacol 3 9% Beer, Lavoris Aldehydes and Ketones Carbonyl Group in Aldehydes and Ketones A carbonyl group in an aldehyde is attached to at least one H atom. in a ketone is attached to two carbon groups. Naming Aldehydes An aldehyde has an IUPAC name in which the e in the alkane name is changed to al. has a common name for the first four aldehydes that use the prefixes: form (1C), acet (2C), propion (3C), and butyr (4C), followed by aldehyde. H C H CH3 C H CH3 CH2 C H methanal ethanal propanal Naming Aldehydes Aldehydes in Flavorings Several naturally occurring aldehydes are used as flavorings for foods and fragrances. Naming Ketones In naming ketones as IUPAC, the e in the alkane name is replaced with one. With a common name, the alkyl groups attached to the carbonyl group are named alphabetically followed by ketone. CH3 C CH3 propanone CH3 C CH2 CH3 2 butanone

6 Properties of Aldehydes and Ketones Physical Properties The polar carbonyl group provides dipole dipole interactions. δ+ δ δ+ δ C= C= Without an H on the oxygen, aldehydes and ketones cannot form hydrogen bonds. Boiling Points Aldehydes and ketones have polar carbonyl groups (C=). δ+ δ C= attractions between polar groups. δ+ δ δ+ δ C= C= higher boiling points than alkanes and ethers of similar mass. lower boiling points than alcohols of similar mass. Comparison of Boiling Points Solubility in Water The electronegative atom of the carbonyl group of aldehydes and ketones forms hydrogen bonds with water. Reactions of Aldehydes & Ketones Aldehydes oxidize readily to carboxylic acids. Ketones do not oxidize further CH3 C H CH3 C H oxidation CH3 C CH3 oxidation N REACTIN

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