大一课件-一下有机化学ch7alcohol,thiol

OrganicforStudentsofMedicineand大学化学III和大学化学April15,hydroxylgroup(－OH硫醇：硫原子取，含巯基,mercaptogroup,or

VitaminHH7.1Structure:C、Oareall E2S

↑↑2P↑↑

SP3

↑SP3杂化轨Classification（3伯醇(一级醇根据官能团所连烃基类型根据烃基结构

仲醇（二级醇）：R2CHOH叔醇（三级醇）：R3COH饱和醇：CH3CH2CH2OH不饱和醇： 芳香醇：

一元醇：CH3CH2OH根据羟基数目

二元醇：

CH

(丙三醇1）Commonalkyl+2）IUPACname

Selectthelongestcontinuouscarbonchainthatcontainsthe–OHgroup.Dropthe–eendingofthecorrespondingalkaneandreplaceitbythesuffix–ol.Indicatethepositionofthe-OHalongthechainbythesmallestpossible

3-methyl-5-hexen-2-2-

Diols:alkanediolTriols:alkanetriol OHOHOHethyleneglycol

HOHOH HOHPhysical

Hydrogen H R

can 亲脂基（疏水基

bondwithChemical C

氧化、脱 酸性（与活泼金属作用作亲核试剂（酯化反应H2O+ NaOH+½HowdoyouAlcoholsasacids:Reactionwithactivemetals.(Na,K,Mg)ROHROH+RONa1/H2ReactionReactionRONaRONa HROH NaOH性HC CH 性

Reactionwithinorganicoxyacids:InorganicEsters和有机酸（以后讨论）成酯。C3C2H+HSH C3C2OS2H+O +HOS2OH

OCH3减压蒸馏CHOSO +H+3 +3or 油glyceryltrinitrateor

+3

浓硫 烈

3H2OAnginapectoris(ischaemicheartdisease) (IsopentylAlkyl3n-OH

P O

烷基一磷酸 烷基二磷酸 烷基三磷酸 P P

O HOH llCCC=HC3H-OOllCCC=HC3H-OOOC许多磷酸酯是剧毒 ， Dehydrationof3Formationofalkenes.Dehydrationof

+CC

+

O

E1

Alkene+ 1ata

morestableC-morestable

C-ObeySaytzeffCH3CHC

CH3CH3CH

CH2CHCH2CHOH

-H2OH+?CH=CHCH2CH3?H+4

2

–+2

CH

+H 2 2

+ CFormationofethers2 ROR+H2醚 +140 主要副反应：分子内脱水成烯烃OxidationofHH

RCHO(醛 RCO(氧化剂：KMn、H2CO4、KO2Oa2C2O7/2SO4、4 HHowdoyoustopattheOStop Stop

NN

CrOchromium Collins’

ORC-R-CH-

BiologicaloxidationofTheoxidativeprocessofalcoholsinlivingorganismstakesplaceintheliver.Theethanolistransformedbytheliverfirsttoacetaldehydeandimmedia thereaftertoaceticacid.Ourbodiescantolerateethanol,uptoacertaindose.Anyexcessalcoholcancauseintoxication.enzyme

CH3C- OCH3C- Acetic

enzyme(2)-UsedbythebodyCH

enzymeOH+

CHC- Antabuse-enzyme(2)complex

Noenzyme(2)oxidizedViolentColourreaction(propertyof1,2-酸性及螯合物的形成多元醇的酸性比一元醇的酸性ROH+NaOH RONa+O

+2

O

＋ CH

+2

CH

绛蓝色 ＋

深蓝色溶Thiolsandrelated ogsofalcohols,R-SH,areknownasthiols,thioalcohols,ormercaptans.Theprefixthio-indicatessulfur.The–SHgroupiscalledasulfhydrylgroup. ethanethiolorWeakH3CCH2 + H3CCH2 +Reactionswithheavymetalions(Hg2+,Pb2+,Cu2+,Ag+) 2

+2

+R-

As

+2,3-

[O] SH

[H] disulfide

H Hydrogenbonding

IUPACDehydrationof