12. Alcohols and Phenols. Based on McMurry s Organic Chemistry, 6 th edition

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1 12. Alcohols and Phenols Based on McMurry s Organic Chemistry, 6 th edition

2 Alcohols and Phenols Alcohols contain an OH group connected to a saturated C (sp 3 ) They are important solvents and synthesis intermediates Phenols contain an OH group connected to a carbon in a benzene ring Methanol, CH 3 OH, called methyl alcohol, is a common solvent, a fuel additive, produced in large quantities Ethanol, CH 3 CH 2 OH, called ethyl alcohol, is a solvent, fuel, beverage Phenol, C 6 H 5 OH ( phenyl alcohol ) has diverse uses - it gives its name to the general class of compounds 2

3 Naming Alcohols General classifications of alcohols based on substitution on C to which OH is attached Methyl (C has 3 H s) Primary (1 ) (C has two H s, one R) Secondary (2 ) (C has one H, two R s) Tertiary (3 ) (C has no H, 3 R s), 3

4 IUPAC Rules for Naming Alcohols Select the longest carbon chain containing the hydroxyl group, and derive the parent name by replacing the -e ending of the corresponding alkane with -ol Number the chain from the end nearer the hydroxyl group Number substituents according to position on chain, listing the substituents in alphabetical order 4

5 Many Alcohols and Phenols Have Common Names 5

6 Naming Phenols Phenol is used both as the name of a specific substance (hydroxybenzene) and as the family name for all hydroxy-substituted aromatic compounds. Name substituents on aromatic ring by their position from OH 6

7 Properties of Alcohols and Phenols: Hydrogen Bonding The structure around O of the alcohol or phenol is similar to that in water, sp 3 hybridized Alcohols and phenols have much higher boiling points than similar alkanes and alkyl halides 7

8 Alcohols and Phenols Form Hydrogen Bonds A positively polarized OH hydrogen atom from one molecule is attracted to a lone pair of electrons on a negatively polarized oxygen atom of another molecule This produces a force that holds the two molecules together These intermolecular attractions are present in solution but not in the gas phase, thus elevating the boiling point of the solution 8

9 Acidity: pk a Values for Typical OH Compounds 9

10 Relative Acidities of Alcohols Simple alcohols are about as acidic as water Alkyl groups make an alcohol a weaker acid The more easily the alkoxide ion is solvated by water the more its formation is energetically favored Steric effects are important 10

11 Inductive Effects Electron-withdrawing groups make an alcohol a stronger acid by stabilizing the conjugate base (alkoxide) 11

12 Generating Alkoxides from Alcohols Alcohols are weak acids require a strong base to form an alkoxide such as NaH, sodium amide NaNH 2, and Grignard reagents (RMgX) Alkoxides are bases used as reagents in organic chemistry 12

13 Phenol Acidity Phenols (pk a ~10) are much more acidic than alcohols (pk a ~ 16) due to resonance stabilization of the phenoxide ion Phenols react with NaOH solutions (but alcohols do not), forming soluble salts that are soluble in dilute aqueous A phenolic component can be separated from an organic solution by extraction into basic aqueous solution and is isolated after acid is added to the solution 13

14 Substituted Phenols Can be more or less acidic than phenol itself An electron-withdrawing substituent makes a phenol more acidic by delocalizing the negative charge Phenols with an electron-donating substituent are less acidic because these substituents concentrate the charge 14

15 Nitro-Phenols Phenols with nitro groups at the ortho and para positions are much stronger acid The pk a of 2,4,6-trinitrophenol is 0.6, a very strong acid 15

16 Preparation of Alcohols: an Overview Alcohols are derived from many types of compounds The alcohol hydroxyl can be converted to many other functional groups This makes alcohols useful in synthesis 16

17 Review: Preparation of Alcohols by Hydration of Alkenes Hydration of an alkene is the addition of H-OH to the C=C to give an alcohol 17

18 Some Reactions of Alcohols Two general classes of reaction At the carbon of the C O bond At the proton of the O H bond 18

19 Dehydration of Alcohols to Yield Alkenes The general reaction: forming an alkene from an alcohol through loss of O-H and H (hence dehydration) of the neighboring C H to give bond Specific reagents are needed 19

20 Acid-Catalyzed Dehydration Tertiary alcohols are readily dehydrated with acid Secondary alcohols require severe conditions (75% H 2 SO 4, 100 C) - sensitive molecules don't survive Primary alcohols require very harsh conditions impractical Reactivity is the result of the nature of the carbocation intermediate 20

21 Acid-Catalyzed Dehydration: mechanism 21

22 Conversion of Alcohols into Alkyl Halides 3 alcohols are converted by HCl or HBr at low temperature 1 and 2 alcohols are resistant to acid use SOCl 2 or PBr 3 by an S N 2 mechanism 22

23 Oxidation of Alcohols Can be accomplished by inorganic reagents, such as KMnO 4, CrO 3, and Na 2 Cr 2 O 7 or by more selective, expensive reagents 23

24 Oxidation of Primary Alcohols To aldehyde: pyridinium chlorochromate (PCC, C 5 H 6 NCrO 3 Cl) in dichloromethane Other reagents produce carboxylic acids 24

25 Oxidation of Secondary Alcohols Effective with inexpensive reagents such as Na 2 Cr 2 O 7 in acetic acid PCC is used for sensitive alcohols at lower temperatures 25

26 Laboratory Preparation of Phenols From aromatic sulfonic acids by melting with NaOH at high temperature Limited to the preparation of alkyl-substituted phenols 26

27 Reactions of Phenols The hydroxyl group is a strongly activating (ortho- and paradirecting) substituent, making phenols substrates for electrophilic halogenation, nitration, sulfonation, and Friedel Crafts reactions Reaction of a phenol with strong oxidizing agents (such as sodium dichromate) yields a quinone (or cyclohexadienedione) Quinones can be easily reduced to hydroquinones (pdihydroxybenzenes) by NaBH 4. OH O Na 2 Cr 2 O 7 H 3 O + Phenol O Benzoquinone 27

28 Quinones in Nature Ubiquinones mediate electron-transfer processes involved in energy production through their redox reactions within the mitochondria of cells they mediate the respiration process in wich electrons are transported from the biological reducing agent NADH to molecular oxygen (+ energy production) 28

29 End of chapter 12 29

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