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