Ch 11 Notes

Ch 11 Notes - Alcohols and Ethers Alcohol: Any kind of...

Info iconThis preview shows pages 1–8. Sign up to view the full content.

View Full Document Right Arrow Icon
Alcohols and Ethers Alcohol: Any kind of R 3 C-OH functional group . Ether: Any kind of R 2 O . POLAR DRUGS NON-POLAR DRUGS Log P Box Log P MOST DRUGS siRNA TAXOL octanol water K ow = [drug] octanol / [drug] water logP = log( K ow ) OH 1-octanol (a primary alcohol) O OH HO HO HO OH ! -D-glucose (a simple sugar) estradiol H OH H H HO (a phenol) (a secondary alcohol) tetrahydrocannabinol logP = 3.8 O OH H H O diethyl ether brevetoxin
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
2 Nomenclature of Alcohols (1) Select the longest continuous chain containing the hydroxyl group as the parent . (2) Drop the "e" in the alkane name and add the suffix " ol ." (3) Number from the end of the chain to give the hydroxyl group the lower number. Examples CH 3 CH 2 CHCH 2 OH CH 3 2 1 2-methyl-1-butan ol CH 3 CH 2 CHCH 2 CH 2 Br OH 3 2 1 1-bromo-3-pentan ol CH 3 CHCH 2 OH C 6 H 5 2 1 2-phenyl-1-propan ol OH CH 3 1 2 3 trans-3-methylcyclohexan ol
Background image of page 2
3 CH 3 C=CH 2 CH 3 + H 2 O H + CH 3 CCH 3 CH 3 OH How to Add H-OH to Alkenes Acid-catalyzed hydration Oxymercuration/ demercuration Hydroboration/ oxidation i. H 2 O, Hg(OCCH 3 ) 2 ii. NaBH 4 , NaOH = alkene oxymercuration product O C-C HO Hg-OCCH 3 O C=C C-C HO H alcohol CH 3 CH 2 CH=CH 2 i. BH 3 -THF ii. H 2 O 2 , NaOH alkene organoborane alcohol [CH 3 CH 2 C H 2 CH 2 ] 3 B CH 3 CH 2 C H 2 CH 2 OH
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
4 Examples of syn-Hydroxylation HO - H 2 O H H OH HO cis -1,2-cyclopentanediol NaHSO 3 H 2 O H H OH HO = - stereochemistry is set Mn O O O O H H H H Os O O O i. OsO 4 ii. NaHSO 3 , H 2 O KMnO 4 cold, dilute
Background image of page 4
5 Reactions of Alcohols There are two general classes of reactions of alcohols: (1) R OH C-O bond breaking (2) RO H O-H bond breaking In (1) the hydroxyl group , or another oxygen function, is the leaving group . In (2) the alcohol acts as an acid . Alcohols as Bases/Nucleophiles alcohols react with strong acids: R O H : : + H-A strong acid R-OH 2 + + A - alkyl oxonium ion
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
6 Alcohols as Bases/Nucleophiles The protonated alcohol function is a much better leaving group than the hydroxyl group. Nucleophiles react with the alkyl oxonium ion in S N 2 reactions: Nu: - + R-OH 2 + S N 2 Nu-R + H 2 O Symmetrical ethers are produced from alcohols in the presence of strong acids: ROH + HA R-OH 2 + + A - ROH + R-OH 2 + : nucleophile S N 2 (-H 2 O) R-O-R H + dialkyl oxonium ion H 2 O R-O-R + H 3 O + symmetrical ether
Background image of page 6
7 Conversion of Alcohols into Mesylates and Tosylates The hydroxyl group, -OH, is a poor leaving group in nucleophilic substitution reactions because the hydroxide ion is a relatively unstable anion.
Background image of page 7

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Image of page 8
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 03/04/2010 for the course CHEM 322AL at USC.

Page1 / 27

Ch 11 Notes - Alcohols and Ethers Alcohol: Any kind of...

This preview shows document pages 1 - 8. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online