Chapter 8. Alcohols, Phenols, and Ethers

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1 Chapter 8. Alcohols, Phenols, and Ethers Alcohol: A compound that has a hydroxyl group ( ) bonded to a saturated, sp 3 - hybridized carbon atom. Phenol: A compound that has a hydroxyl group bonded to an aromatic ring. Ether: A compound that has an oxygen atom bonded to two organic groups. 8.1 Naming Alcohols, Phenols, and Ethers Alcohols C C C A primary alcohol (1 o ) A secondary alcohol (2 o ) A tertiary alcohol (3 o ) Simple alcohols are named in the IUPAC system as derivatives of the parent alkane, using the suffix ol. Step 1. Select the longest carbon chain containing the hydroxyl group, and replace the e ending of the corresponding alkane with ol. Step 2. Number the carbons of the parent chain beginning at the end nearer the hydroxyl group. Step 3. Number all substituents according to their position on the chain, and write the name listing the substituents in alphabetical order. 3 C 1 2 CC C 5 2 C 3 C 3 2-Methylpentan-2-ol cis-cyclohexane-1,4-diol 4 3 C 3 C CC phenylbutan-2-ol C 2 Phenylmethanol (Benzyl alcohol) C 3 3 C C C 2 C 2 C 2 CC 2 C 3 2-Methylpropan-2-ol (tert-butyl alcohol) Ethane-1,2-diol (Ethylene glycol) Propane-1,2,3-triol (Glycerol) Phenols Phenols are named as substituted aromatic compounds with phenol used as the parent name rather than benzene. 1

2 3 C m-methylphenol 2 N N 2 2,4-Dinitrophenol Ethers Simple ethers that contain no other functional groups are named by identifying the two organic groups and adding the word ether. 3 C C 3 3 C C 3 tert-butyl methyl ether C2 C 3 Ethyl phenyl ether If more than one ether linkage is present, or if other functional groups are present, the ether part is named as an alkoxy substituent on the parent compound. 2 3 C C C 1 3 C C 3 C 3 p-dimethoxybenzene 4-tert-Butoxycyclohexene 8.2 Properties of Alcohols, Phenols, and Ethers: ydrogen Bonding bp o C 0.5 o C 12.3 o C C 3 8 Mol. Wt.: C 4 10 Mol. Wt.: Cl C 2 5 Cl Mol. Wt.: Alcohols and phenols have unusually high boiling points due to the hydrogen bonding in the liquid state. The positively polarized hydrogen of one molecule is attracted to the negatively polarized oxygen of another molecule. δ δ+ δ+ δ δ δ+ δ δ+ 2

3 8.3 Properties of Alcohols and Phenols: Acidity Alcohols and phenols are both weakly basic and weakly acidic. As weak bases, alcohols and phenols are reversibly protonated by strong acids to yield oxonium ions, X + X As weak acids, alcohols and phenols dissociate to a slight extent by donating a proton to water, generating 3 + and an alkoxide ion ( ) Alcohols react with alkali metals to yield Metal alkoxide that are strong bases. 2 C Na 2 C 3 Na + 2 C 3 C C C + 2 K 2 3 C C K + 2 C 3 C 3 Phenols are about a million times more acidic than alcohols (phenols are soluble in dilute aqueous Na, but alcohols are not). Phenoxide anion is resonance-stabilized by the aromatic ring. 8.4 Synthesis of Alcohols Alcohols can be prepared by hydration of alkenes following the Markovnikov rule. 2 2 S 4 catalyst eduction of Aldehydes and Ketones Aldehydes are converted into primary alcohols, and ketones are converted into secondary alcohols. Sodium borohydride, NaB 4, is usually chosen because of its safety and ease of handling. 3

4 C C 1. NaB 4, ethanol C 85% 1 o alcohol 1. NaB 4, ethanol C % 2 o alcohol eduction of Esters and Carboxylic Acids Esters and carboxylic acids are reduced to give primary alcohols. These reductions proceed more slowly than the corresponding reductions of aldehydes and ketones, so the more powerful reducing agent LiAl 4 is used. Two hydrogens are added to the carbonyl carbon during the reduction. C 3 (C 2 ) 7 C C(C 2 ) 7 C 1. LiAl 4, ether C 3 (C 2 ) 7 C C(C 2 ) 7 C 2 87% C 3C 2 C CCC 3 1. LiAl 4, ether C 3 C 2 C CC 2 91% + C eaction of Alcohols 1. Dehydration of Alcohols elimination of 2 to give alkenes. Treatment of secondary and tertiary alcohols with a strong acid. C 3 2 S 4, 2 50 o C C % 2 C 3 C The mechanism is E1 process: Strong acid protonates the alcohol oxygen, the protonated intermediate spontaneously loses water to generate a carbocation, and a loss of + from the neighboring carbon atom yield the alkene product. 4

5 Acid-catalyzed dehydrations follow Zaitsev s rule, giving the more highly substituted alkene as major product. C 3 C 2 C C 3 C 3 2 S 4, 2 25 o C C 3 C 3 C 3 C CC 3 + C 3 C 2 C C 2 major minor 2. xidation of Alcohols Primary alcohols give aldehydes (non-aqueous condition: PCC, PDC in C 2 Cl 2 ) or carboxylic acids (aqueous acidic condition), secondary alcohols give ketones, but tertiary alcohols don t normally react with oxidizing agents. PCC C 3 (C 2 ) 5 C 2 C C 2 Cl 3 (C 2 ) 5 C 78% 2 C 3 (C 2 ) 8 C 2 Cr C 3 (C 2 ) 8 C 93% Na 2 Cr 2 7 2, C 3 C 2 91% PCC: pyridinium chlorochromate (C 5 6 NCr 3 Cl) 3. Conversion into Ethers Williamson ether synthesis Alcohols are converted into ethers by formation of the corresponding alkoxide ion followed by reaction with an alkyl halide (S N 2 process). + C 3 I C 3 + I 74% eaction of the more hindered alkoxide with the less hindered alkyl halide works best. S N 2 + C 3 I C 3 + I E2 C 3 C 3 + C 2 C Cl + C 3 + Cl C 3 5

6 8.6 Synthesis and eactions of Phenols Synthesis of Phenols An aromatic compound is first sulfonated by treatment with S 3 / 2 S 4, and the resulting sulfonic acid is then converted into a phenol by high-temperature reaction with Na. S 3 S 3 2 S 4 1. Na 300 o C % 1. Alcohol-Like eactions of Phenols + C 3 C 2 C 2 C 2 Br N 2 K 2 C 3 Acetone C 2 C 2 C 2 C 3 N 2 80% owever, phenols can t be dehydrated by treatment with acid and can t be converted into halides by treatment with X. 2. Electrophilic Aromatic Substitution eactions of Phenols The group is an activating, ortho- and para-directing substituent in electrophilic aromatic substitution reactions. alogenation, Nitration, and Sulfonation. N 3 FeBr 2 S 4 3 N 2 Br Br 2 S 3 2 S 4 S 3 3. xidation of Phenols: Quinones Treatment of a phenol with a strong oxidizing agent such as sodium dichromate (Na 2 Cr 2 7 ) yields a cyclohexadienedione, or quinone. Quinones can be easily reduced to hydroquinones (p-dihydroxybenzenes) by NaB 4 or SnCl 2, and hydroquinones can be easily oxidized back to quinones by Na 2 Cr

7 Na 2 Cr NaB 4 Na 2 Cr 2 7 Benzoquinone ydroquinone Ubiquinones biochemical oxidizing agents in electron-transfer processes. Ubiquinones mediate the respiration process in which electrons are transported from NAD to molecular oxygen to give NAD + and water. Energy is produced through the process. C 3 C 3 C 3 C 3 NAD NAD + C 3 C Synthesis and eactions of Ethers Synthesis of Ethers Conversion of alcohols to alkoxide ions followed by S N 2 reaction with a primary alkyl halide. Na or K 'X M ' S N 2 eactions of Ethers Ethers are unreactive to most common reagents (halogens, mild acids, bases, and nucleophiles) ethers are widely used as reaction solvents. Ethers are cleaved by strong acids such as aqueous I or Br by either an S N 1 or S N 2 pathway, depending on the structure of the ether. You can tell the mechanism by the product analysis. S N 2 cleavage primary and secondary alkyl groups Nucleophilic halide ion attacks the protonated ether at the less hindered site. The ether oxygen atom stays with the more hindered alkyl group. 7

8 S N 1 cleavage tertiary alkyl groups (stable carbocation intermediates) The ether oxygen atom stays with the less hindered alkyl group, and the halide bonds to the tertiary group. Examples C 3 C C 3 C 2 C 3 I C 3 C C 2 C 3 C 3 I S N 2 C 3 C + I C 2 C 3 C 3 more hindered less hindered Br Br, 2 S N 1 Br Br + Br less hindered more hindered 8.8 Epoxides Angle strain in the three-membered ring gives higher reactivity than acyclic ethers. Naming Use the name of the parent alkene followed by oxide, or Use the name of the parent alkane with an epoxy prefix. propylene oxide ethylene oxide Et 1,2-epoxy-2-methylpropane 1,2-epoxybutane Preparation eaction of an alkene with a peroxyacid, C 3. Cl MCPBA C 2 Cl 2, 25 o C 78% + Cl eaction ing cleavage by dilute aqueous acid to give a 1,2-diol. Acid-catalyzed epoxide cleavage takes place by S N 2 attack of 2 on the protonated epoxide. 8

9 S N % 8.9 Thiols and Sulfides Thiols, S, are sulfur analogs of alcohols; sulfides, S, are sulfur analogs of ethers. Naming Thiols are named in the same way as alcohols, with the suffix thiol used in place of ol. The S group is referred to as a mercapto group. C 3 C 2 S S 2 C S Ethanethiol Cyclohexanethiol p-mercaptobenzoic acid Sulfides are named in the same way as ethers, with sulfide used in place of ether. The prefix alkylthio is used in place of alkoxy for more complex substances. C 3 S C 3 S C 3 S C 3 dimethyl sulfide Methyl phenyl sulfide 3-(Methylthio)cyclohexene Preparation Thiols can be prepared by the S N 2 reaction of hydrosulfide anion, S, with alkyl halide. C 3 (C 2 ) 6 C 2 Br + Na S C 3 (C 2 ) 6 C 2 S + NaBr Sulfides are prepared by treating a primary or secondary alkyl halide with a thiolate ion, S. S Na + C 3 I S C3 + NaI 96% 9

10 Thiols can be oxidized by bromine to yield disulfides, and disulfides can be reduced back to thiols by treatment with zinc metal and acetic acid. 2 S Br 2 Zn, + S S + 2 Br 10

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