AlcoholsAlcohols

Nomenclature of alcohols:Nomenclature of alcohols:IUPAC systemIUPAC system

اسم اسم نذكر حرف alkanealkane نذكر منه نحذف حرف و منه نحذف ب eeو نستبدله ب و نستبدله olol و

مجموعة يعطى الذي الطرف من نعد الترقيم حالة في مجموعة و يعطى الذي الطرف من نعد الترقيم حالة في وOHOH ترقيم ترقيم أقل أقل

حالة حالة في حرف alkene or alkynealkene or alkyneفي حرف نحذف نستبدله ee نحذف نستبدله و وololب ب

يعطى الذي الطرف من نعد الترقيم حالة في يعطى و الذي الطرف من نعد الترقيم حالة في وترقيم OHOHمجموعة مجموعة ترقيم أقل أقل

Examples

Common namesCommon names اسم اسم نذكر ب alkylalkylنذكر ب المتصلة كلمة OHOHالمتصلة نكتب كلمة ثم نكتب alcoholalcoholثم

Examples

Carbinol methodCarbinol method

أن على الطريقة هذه أن تعتمد على الطريقة هذه ب CH3OHCH3OHتعتمد ب يسمى يسمىCarbinolCarbinol تسمى تسمى و بذكر alcoholsalcohols و منه بذكر كمشتقات منه كمشتقات

في alkylalkylأسماء أسماء الهيدروجين ذرات من بدال في المستبدلة الهيدروجين ذرات من بدال المستبدلةكلمة CH3CH3مجموعة مجموعة نكتب كلمة ثم نكتب CarbinolCarbinolثم

ExamplesExamples

IUPAC nameIUPAC name 2-propen-1-ol2-propen-1-ol 2-Butanol 2-Butanol 2-Methyl-1-Propanol2-Methyl-1-Propanol

Common nameCommon name Allyl alcohol Allyl alcohol Sec-Butyl alc. Sec-Butyl alc. Isobutyl alc. Isobutyl alc.

Carbinol methodCarbinol method Vinyl carbinol Vinyl carbinol Ethyl methyl Ethyl methyl carbinolcarbinol

Isopropyl carbinol Isopropyl carbinol

Examples of nomenclature

Classification of alcoholsClassification of alcohols

According to number of OH groupsAccording to number of OH groups• MonohydroxyMonohydroxy alcohols: which contain one OH group e.g. alcohols: which contain one OH group e.g.

ethanolethanol• DihydroxyDihydroxy alcohols: which contain two OH group e.g. alcohols: which contain two OH group e.g.

ethyleneglycol.ethyleneglycol.• PolyhydroxyPolyhydroxy alcohols: which contain more than two OH alcohols: which contain more than two OH

groups e.g. glycerol and carbohydrate.groups e.g. glycerol and carbohydrate.

According to number of OH groupsAccording to number of OH groups Monohydroxy alcohols are classified according to type of Monohydroxy alcohols are classified according to type of

carbon bearing OH into three types:carbon bearing OH into three types:

• 1ry alcohols: in which OH attach with 1ry carbon e.g. 1ry alcohols: in which OH attach with 1ry carbon e.g. RCH2OHRCH2OH

• 2nd alcohols: in which OH attach with 2nd carbon e.g. R2 2nd alcohols: in which OH attach with 2nd carbon e.g. R2 CHOHCHOH

• t-alcohols : in which OH attach with tertiary carbon e.g. t-alcohols : in which OH attach with tertiary carbon e.g. R3COHR3COH

Preparation of alcoholsPreparation of alcohols a) Preparation of 1ry alcohol1. a) Preparation of 1ry alcohol1. 1- Hydrolysis of alkene1- Hydrolysis of alkene

2 .Hydrolysis of alkyl halide

E.g. conversion of benzene to benzyl alcoholE.g. conversion of benzene to benzyl alcohol

3 .Reduction of carbonyl compound

Reduction of aldehyde gives 1ry alcohol, while of ketone gives 2nd alcohol

NaBH4 reduce C=O and not reduce C=CNaBH4 reduce C=O and not reduce C=C

e.g. e.g. CH3CH=CH-CHO + NaBH4 CH3CH=CH-CH2 OH CH3CH=CH-CHO + NaBH4 CH3CH=CH-CH2 OH

Crotonaldehyde 2-Butenol Crotonaldehyde 2-Butenol

4 .Reduction of acids and esters

Acids and esters are reduced to 1ry alcohol by use of LiAlH4

E.g. CH3COOH + LiAlH4 CH3CH2OH

CH3COOCH2CH3 + LiAlH4 2 CH3CH2OH

Also Na/ROH can reduce esters to 1ry alcohol

Grignard reagent is used to prepare 1ry, 2nd, and t-alcohols

a) Preparation of 1ry alcohol

1ry alcohol is prepared from Grignard reagent and formaldehyde

Grignard reagent can be prepared as follow:

bb) ) Preparation of secondary alcoholsPreparation of secondary alcohols

Secondary alcohols are prepared from Grignard reagent and aldehyde other than formaldehyde.

cc) ) Preparation of tertiary alcoholsPreparation of tertiary alcohols

Tertiary alcohols are prepared from Grignard reagent and ketones.

Grignard reagent is used to synthesis many organic Grignard reagent is used to synthesis many organic compounds ecompounds e..gg..

Reactions of alcoholsReactions of alcohols

1)Replacement of OH by halogen1)Replacement of OH by halogen

a) By reaction with HXa) By reaction with HX

ROH + HX RX + H2OROH + HX RX + H2O

X= I, Br and ClX= I, Br and Cl

e.g. CH3CH2OH + HBr CH3CH2Br +HOHe.g. CH3CH2OH + HBr CH3CH2Br +HOH

b) By reaction with phosphorus halide

R OHPCl5

R Cl + HCl + POCl3

R OHSOCl2

R Cl + HCl + SO2

R OHPCl3

3 R Cl3 + H3PO3

Dehydration of alcoholsDehydration of alcoholsSee alkeneSee alkene

Formation of estersFormation of esterse.g. CH3CH2OH + CH3COOH CH3COOCH2CH3 + H2Oe.g. CH3CH2OH + CH3COOH CH3COOCH2CH3 + H2O

Ethanol acetic acid Ethyl acetate

Differentiation between different types of alcohols1. By oxidation

a)a) 1ry alcohol oxidize to give aldehyde or acid1ry alcohol oxidize to give aldehyde or acid

RCH2OH[O]

RCHOaldehyde

[O]RCOOH

acide.g.

CH3CH2CH2OH

propan-1-ol

[O]CH3CH2CHO

propionaldehyde

[O]CH3CH2COOH

propionic acid

Examples of oxidizing agent are K2Cr2O7/ Examples of oxidizing agent are K2Cr2O7/ H2SO4, KMnO4 and H2SO4, KMnO4 and Cu/250oCCu/250oC

b)2nd alcohol oxidize to give ketoneb)2nd alcohol oxidize to give ketone

c) Tertiary alcohols do not oxidizec) Tertiary alcohols do not oxidize

Iodoform test

This reaction occurs with alcohols containing

Also aldehydes or ketones containing CH3-CO can give iodoform

Examples of iodoform equationsExamples of iodoform equations

Mechanism of iodoformMechanism of iodoform

(a) For alcohols(a) For alcohols

(b) For aldehyde and ketones(b) For aldehyde and ketones

Only one aldehyde can give iodoform, this aldehyde is Only one aldehyde can give iodoform, this aldehyde is acetaldehyde, the mechanism of aldehyde and ketones are acetaldehyde, the mechanism of aldehyde and ketones are step 2, and 3 in alcohol.step 2, and 3 in alcohol.

E.g. acetoneE.g. acetone

EthersEthers

Nomenclature of ethersNomenclature of ethers

IUPAC nomenclatureIUPAC nomenclature

تسمى تسمىRORO ب بAlkoxyAlkoxy باعتبار التسمية تتم باعتبار و التسمية تتم فرع فرع RORO وااللكان سلسلة االلكان في سلسلة في

E.g. E.g. CH3O-CH3O- CH3CH2O-CH3CH2O- CH3CH2CH2CH2O- CH3CH2CH2CH2O- MethoxyMethoxy Ethoxy ButoxyEthoxy Butoxy

Examples of ethersExamples of ethers CH3OCH2CH2CH3 CH3CH2OCH2CH3

1-Methoxypropane Ethoxyethane

Comman NomenclatureComman Nomenclature أسماء أسماء نذكر كلمة ألألللاانذكر نكتب ثم األوكسجين بذرة المتصلة كلمة كيل نكتب ثم األوكسجين بذرة المتصلة كيل

etherether

Examples Examples

CH3CH2OCH2CH3 C6H5OCH3 (CH3) 3 C-OCH2CH3CH3CH2OCH2CH3 C6H5OCH3 (CH3) 3 C-OCH2CH3

Diethyl ether methyl phenyl ether t-Butyl ethyl Diethyl ether methyl phenyl ether t-Butyl ethyl

ether (Anisole)ether (Anisole)

Preparation of ethersPreparation of ethers From alcoholsFrom alcohols

Wiliamson synthesisWiliamson synthesis

It is reaction between alkoside and alkyl halideIt is reaction between alkoside and alkyl halide

E.g. preparation of diethyl etherE.g. preparation of diethyl ether

QuestionQuestion Show how could you prepare the following ethers:Show how could you prepare the following ethers:

(a) Anisole (phenyl methyl ether) (b) t- butyl ethyl et (a) Anisole (phenyl methyl ether) (b) t- butyl ethyl et

AnswerAnswer

Observation:Observation: Alkyl halide must be primary or secondary because t-alkyl halide Alkyl halide must be primary or secondary because t-alkyl halide

undergoes loss of HCl (elimination) so it gives alkene not ether e.g.undergoes loss of HCl (elimination) so it gives alkene not ether e.g.

Reaction of ethersReaction of ethers

Reaction with acid halideReaction with acid halide

Cyclic ethersCyclic ethers

تسمى تسمىCyclic ethersCyclic ethers ب بalkene oxidealkene oxide ذرتي رقمي نحدد ذرتي أو رقمي نحدد أوب يسميا و األوكسجين بذرة المتصلتين ب الكربون يسميا و األوكسجين بذرة المتصلتين و و epoxyepoxyالكربون

ل ل ينسبا alkanealkaneينسبا

Preparation of cyclic ethersPreparation of cyclic ethers

In case of unsymmetrical cyclic ethers, the product depends on the reaction condition

In case of acidic medium, nucleophile goes to more steric carbon i.e. carbon containing less number of hydrogen.

In case of basic medium, nucleophile goes to less steric carbon i.e. carbon containing great number of hydrogen.

Examples