3 Naming Alcohols The names of alcohols in IUPAC replace the -e with -ol.with common names use the name of the alkyl groupfollowed by alcohol.Formula IUPAC Common NameCH4 methaneCH3─OH methanol methyl alcoholCH3─CH3 ethaneCH3─CH2─OH ethanol ethyl alcohol
4 More Names of AlcoholsIUPAC names for longer chains number the chain from the end nearest the -OH group.CH3─CH2─CH2─OH propanolOH│CH3─CH─CH2─CH butanolCH OH│ │CH3─CH─CH2─CH2─CH─CH methyl-2-hexanol
8 Phenols in Medicine Phenol is the IUPAC name for benzene with a hydroxyl group.is used in antiseptics and disinfectants.phenol resorcinol hexylresorcinol
9 Derivatives of PhenolCompounds of phenol are the active ingredients in the essential oils of cloves, vanilla, nutmeg, and mint.
10 Naming Phenols To name a phenol with two substituents, assign C-1 to the carbon attached to the –OH.number the ring to give the lowest numbers.11343-chlorophenol bromophenol
11 Learning Check Write the structure of each of the following. A pentanolB. ethyl alcoholC methylphenol
12 Solution Write the structure of the following. A. 3-pentanol OH | CH3—CH2—CH—CH2—CH3B. ethyl alcohol CH3—CH2—OHC. 4-methylphenolOHC3
13 Classification of Alcohols Classification of alcohols isdetermined by the number of alkyl groups attached to the carbon bonded to the hydroxyl.primary (1°), secondary (2°), or tertiary(3).Primary (1º) Secondary (2º) Tertiary (3º) 1 group groups 3 groups H CH CH | | |CH3—C—OH CH3—C—OH CH3—C—OH | | | H H CH3
14 Learning Check 1) primary, 2) secondary, or 3) tertiary. OH | Classify each alcohol as1) primary, 2) secondary, or 3) tertiary.OH|A. CH3—CH—CH2—CH3B. CH3—CH2—CH2—OHC. CH3—CH2—C—CH2—CH3CH3
15 Solution | A. CH3—CH—CH2—CH3 secondary B. CH3—CH2—CH2—OH primary C. CH3—CH2—C—CH2—CH3 tertiaryCH3
17 Thiols Thiols often have strong odors. are used to detect gas leaks. are found in onions, oysters, and garlic.
18 Ethers An ether contains an ─O─ between two carbon groups. has a common name that gives the alkyl names of the attached groups followed by ether.CH3─O─CH3 CH3─CH2─O─CH3dimethyl ether ethyl methyl ether
19 Learning Check Write the structure of the following. A. 3-pentanol B. diethyl ether
20 Solution OH | A. 3-pentanol CH3─CH2─CH─CH2─CH3 B. diethyl ether CH3─CH2─O─CH2─CH3
21 Ethers as Anesthetics Anesthetics inhibit pain signals to the brain. like diethyl ether CH3─CH2─O─CH2─CH3 were used for over a century, but caused nausea and were flammable.developed by the 1960’s were nonflammable.Cl F F Cl F H│ │ │ │ │ │H─C─C─O─C─H H─C─C─O─C─HF F F H F HEthane(enflurane) Penthrane
22 MTBE Methyl tert-butyl ether CH3 │ CH3─O─C─CH3 is second in production of organic chemicals.is an additive used to improve gasoline performance.use is questioned since the discovery that MTBE has contaminated water supplies.
31 Dehydration of Alcohols Alcohols undergodehydration when heated with an acid catalyst.the loss of —H and —OH from adjacent carbon atoms.H OH| | H+, heatH—C—C—H H—C=C—H + H2O| | | |H H H Halcohol alkene
32 Learning CheckWrite the equations for the reaction of 2-propanol when itundergoes1. combustion.2. dehydration.
36 Oxidation of Primary (1) Alcohols When a primary alcohol is oxidized, [O],one H is removed from the –OH.another H is removed from the carbon bonded to the OH.an aldehyde is produced.[O]Primary alcohol AldehydeOH O| [O] ||CH3—C—H CH3—C—H + H2O|HEthanol Ethanal(ethyl alcohol) (acetaldehyde)
37 Oxidation of Secondary (2) Alcohols When a secondary alcohol is oxidized, [O],one H is removed from the –OH.another H is removed from the carbon bonded to the OH.a ketone is produced.[O]secondary alcohol ketoneOH O│ [O] ║CH3─C─CH CH3─C─CH3 + H2O│H2-propanol (isopropyl alcohol) propanol (dimethyl ketone)
38 Oxidation of Tertiary ( 3)Alcohols Tertiary 3alcohols do not readily oxidize [O]Tertiary alcohol no reactionOH│ [O]CH3─C─CH3 no product│CH no H on the C-OH to oxidize2-methyl-2-propanol
39 Oxidation of Ethanol in the Body enzymes in the liver oxidize ethanol.aldehyde product impairs coordination.blood alcohol over 0.4% can be fatal O O║ ║CH3CH2OH CH3CH CH3COH CO2 + H2Oethyl alcohol acetaldehyde acetic acid
40 Ethanol CH3CH2OH 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.
43 Oxidation of Thiols When thiols undergo oxidation, an H atom is lost from each of two –SH groups.the product is a disulfide.[O]CH3─SH + HS─CH CH3─S─S─CH3 + H2O
44 Learning Check OH │ [O] CH3─CH─CH2─CH3 O ║ Select the product for the oxidation ofOH│ [O]CH3─CH─CH2─CH3O ║1) CH3─CH=CH─CH ) CH3─C─CH2 ─CH3│3) CO2 + H2O ) CH3─CH─CH2─CH3
45 Solution OH │ [O] CH3─CH─CH2─CH3 O ║ 2) CH3─C─CH2 ─CH3 Select the product for the oxidation ofOH│ [O]CH3─CH─CH2─CH3O ║2) CH3─C─CH2 ─CH3
46 Learning Check A) H+, heat B) [O] C) + O2 1) CH3—CH=CH2 2) CO2 + H2O O Select the product when CH3—CH2—CH2—OH undergoes each of the following reactions:A) H+, heat B) [O] C) + O21) CH3—CH=CH22) CO2 + H2O O||3) CH3—CH2—C—H
47 Solution O [O] || B. 3) CH3—CH2—C—H C. + O2 2) CO2 + H2O A. H+, heat 1) CH3—CH=CH2O[O] ||B ) CH3—CH2—C—HC. + O2 2) CO2 + H2O
48 Chapter 12 Organic Compounds with Oxygen and Sulfur 12.4Aldehydes and Ketones
49 Carbonyl Group in Aldehydes and Ketones A carbonyl groupin an aldehyde is attached to at least one H atom.in a ketone is attached to two carbon groups.
50 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.O O O║ ║ ║H─C─H CH3─C─H CH3─CH2─C─Hmethanal ethanal propanal(formaldehyde) (acetaldehyde) (propionaldehyde)
52 Aldehydes in Flavorings Several naturally occurring aldehydes are used as flavorings for foods and fragrances.Benzaldehyde (almonds)Cinnamaldehyde (cinnamon)
53 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 followedby ketone.O O║ ║CH3 ─C─CH CH3─C─CH2─CH3 propanone butanone(dimethyl ketone) (ethyl methyl ketone)
54 Ketones in Common Use Nail polish remover, solvent Propanone, Dimethylketone, AcetoneButter flavoring
55 Learning Check Classify each as 1) aldehyde or 2) ketone. O O || || || ||A. CH3—CH2—C—CH B. CH3—C—HCH O| ||C. CH3—C—CH2—C—H D.|CH3
57 Learning Check Classify each as an 1) aldehyde 2) ketone 3) alcohol or 4) ether.O║A. CH3─CH2─C─CH3 B. CH3─O─CH3CH O OH│ ║ │C. CH3─C─CH2─C─H D. CH3─CH ─CH3│CH3
58 Solution O ║ A. CH3─CH2─C─CH3 B. CH3─O─CH3 2) ketone 4) ether CH3 O OH │ ║ │C. CH3─C─CH2─C─H D. CH3─CH─CH3│CH31) aldehyde ) alcohol
59 Learning Check Name each of the following. O ║ 1. CH3─CH2─CH2─CH2─C─H 2. Cl─CH2─CH2─C─H3. CH3─CH2─C─CH3
60 Solution Name each of the following: O ║ 1. CH3─CH2─CH2─CH2─C─H pentanal2. Cl─CH2─CH2─C─H 3-chloropropanal3. CH3─CH2─C─CH3 2-butanone;ethyl methyl ketone
61 Learning Check Name the following compounds. O || A. CH3—CH2—CH2—C—CH B.CH O| ||C. CH3—C—CH2—C—H|CH3
62 Solution A. 2-pentanone; methyl propyl ketone B. cyclohexanone C, 3,3-dimethylbutanal
63 Learning Check Draw the structural formulas for each: A. 4-methylpentanalB. 2,3-dichloropropanalC. 3-methyl-2-butanone
64 Solution Draw the structural formulas for each: CH3 O │ ║ A. 4-methylpentanal CH3─CH─CH2─CH2─C─HCl O│ ║B. 2,3-dichloropropanal Cl─CH2─CH─C─HCH3 OC. 3-methyl-2-butanone CH3─CH─C─CH3
65 Chapter 12 Organic Compounds with oxygen and Sulfur 12.5Properties of Aldehydes and Ketones
66 Physical PropertiesThe polar carbonyl group provides dipole-dipole interactions.+ + -C=O C=OWithout an H on the oxygen, aldehydes and ketones cannot form hydrogen bonds.
67 Boiling Points + - + - + - Aldehydes and ketones have polar carbonyl groups (C=O).+ -C=Oattractions between polar groups.+ + -C=O C=Ohigher boiling points than alkanes and ethers of similar mass.lower boiling points than alcohols of similar mass.
69 Solubility in WaterThe electronegative O atom of the carbonyl group of aldehydes and ketones forms hydrogen bonds with water.
70 Learning Check Indicate if each is soluble or insoluble in water. A. CH3—CH2—CH3B. CH3—CH2—OHO||C. CH3—CH2—CH2—C—HD. CH3—C—CH3
71 Solution Indicate if each is soluble or insoluble in water. A. CH3—CH2—CH3 insolubleB. CH3—CH2—OH solubleO||C. CH3—CH2—CH2—C—H solubleD. CH3—C—CH soluble
72 Tollens’ Test In Tollens’ test, Tollens’ reagent, which contains Ag+, oxidizes aldehydes, but not ketones.Ag+ is reduced to metallic Ag, which appears as a “mirror” in the test tube.
73 Benedict’s Test In the Benedict’s test, Benedict’s reagent, which contains Cu2+, reacts with aldehydes that have an adjacent OH group.An aldehyde is oxidized to a carboxylic acid, while Cu2+ is reduced to give red Cu2O(s).
74 Learning Check Write the structure and name of the oxidized product when each is mixed with Tollens’ reagent.A. butanalB. acetaldehydeC. ethyl methyl ketone
75 Solution A. butanal O || CH3—CH2—CH2—C—OH butanoic acid B. acetaldehyde OCH3—C—OHacetic acidC. ethyl methyl ketone None.Ketones are not oxidized by Tollen’s reagent.
81 Learning CheckIdentify each as a chiral or achiral compound.ACH23lBr
82 Solution chiral achiral chiral A C H l B r Identify each as a chiral or achiral compound.chiral achiral chiralACH23lBr
83 Fischer Projections A Fischer projection is a 2-dimensional representation of a 3-dimensional molecule.places the most oxidized group at the top.uses vertical lines in place of dashes for bonds that go back.uses horizontal lines in place of wedges for bonds that come forward.