上海交通大学：《有机化学》教程教学资源（英文讲稿）08 Alcohols. ethers and phenols

p265 8 Alcohols. ethers and phenols 0—H OH (ArO-RR,Ar

8: Alcohols, Ethers, and Phenols p.265 R(Ar) O R(R', Ar) O C H OH

8. 1 Naming Alcohols, Phenols, and ethers Alcohols Methyl( c has 3 Hs), primary (1 )(C has two HS, one R), secondary( 2)(c has one H, twoR’s), tertiary③3°)( C has no H,3R’s)

8.1 Naming Alcohols, Phenols, and Ethers 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), Alcohols:

IUPAC Rules for Naming Alcohols CH HO H OH CHCHCHg 12|345 CHaCCHCHOCH OH CH HO H 2.Methyl-2-pentanol cis-1, cYclohexanediol 3-Pheny1-2-butanol 92004 Thomson/Brooks Cole 乙醇脱氢酶 乙醛脱氢酶 CH3- CH-oh CH3-c-H CH2-C-Ooh CH3-OH—-H-CH H-C-OH

IUPAC Rules for Naming Alcohols 乙醇脱氢酶 CH3 CH2 OH CH3 OH CH3 C H O H C H O CH3 C OH O H C OH O 乙醛脱氢酶

OH OH geraniol((香叶醇) cedro(柏木脑醇) OAC OH Taxol H OH OH OCOPh OAc Nicolaou k.c. nature Holton.j. amer. Chem. soc

Ph N O O O O O OH OH OH Ph OH OAc OAc OCOPh H Taxol OH geraniol(香叶醇) OH cedrol(柏木脑醇) Nicolaou K.C. Nature Holton R. J. Amer. Chem. Soc

OH 1-CH-CH2NHC(CH3)3.HCI Clenbuterol(羟甲叔丁肾上腺素;瘦肉精) HO OH HO CH-CHONH 肾上腺素

CH CH2NHC(CH3 ) H2N 3 Cl Cl OH .HCl Clenbuterol(羟甲叔丁肾上腺素;瘦肉精) CH CH2NH2 OH HO HO 肾上腺素

8.2 Properties of Alcohols, phenols and Ether: Hydrogen bonding hybridized I Alkanes, Rh Chloroalkanes. RCI Alcohols, ROH 287 299 10 0 R=(-0c1(-(

8.2 Properties of Alcohols, Phenols and Ether : Hydrogen Bonding • sp3 hybridized p.271, 287, 299

Alcohols form Hydrogen Bonds 1.085mm H HRQ H(R O O-Q-4 0--O O H(R 0096nm R

Alcohols Form Hydrogen Bonds H(R) O H H O H(R) H O H H O H H O H(R) H O R H O H O H H 0.096 nm 1.085 nm

272 8.3 Properties of Alcohols and Phenols: Acidity O-y RO +h

8.3 Properties of Alcohols and Phenols: Acidity p.272 R O H RO- + H +

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

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

p.14,389 Inductive effects F H R-C-Oh>R-C-OH F H Electron-withdrawing CF CH3 groups stabilize alkoxide and CF <C-0- versus CH -C-0 lower pKa CF CH3 pKa= 5.4 pKa =18 @2004 Thomson/Brooks Cole

• Inductive effects p.14, 389 R C F F OH R C H H > OH