Carboxylic acids R-COOH

Carboxylic acidsCarboxylic acids RR--COOHCOOH

NomenclatureNomenclature

AA) ) IUPACIUPACاسم - - اسم نأخذ حرف alkane alkane نأخذ حرف ونحذف بـ ee ونحذف بـ ونستبدله ..oic acidoic acid ونستبدله

AlkaneAlkane alkanoic acidalkanoic acidترقيم مراعاة ترقيم مع مراعاة 11 كرقمكرقم COOHCOOH-- مع ..

BB) ) Common nameCommon name

الحروف - الترقيم استخدام من بدًال5 يمكن، αالالتينية β ، γ ، δ

Nomeclature of some aromatic acidsNomeclature of some aromatic acids

Preparation of carboxylic acidsPreparation of carboxylic acids

(1) Oxidation of 1ry alcohols or aldehydes(1) Oxidation of 1ry alcohols or aldehydes

Oxidizing agent may KMnO4, K2Cr2O7

(2) (2) From Grignard reagentFrom Grignard reagent

(3(3Oxidation of alkyl benzeneOxidation of alkyl benzene

4) Hydrolysis of nitriles4) Hydrolysis of nitrilesNitrile means compounds containing CNNitrile means compounds containing CN

ذر - - عدد لزيادة تصلح الطريقة ذر هذه عدد لزيادة تصلح الطريقة ذرة ااهذه مركب أى ذرة ت مركب أى تكاآلتى : واحدة كاآلتى :كربون واحدة كربون

e.g. convert n-propanol to butanoic acid

((55)From olefins )From olefins ((alkenes)alkenes)

(6) From acetylenes

(7) Haloform reaction

Reaction of carboxylic acidsReaction of carboxylic acids

11)) Formation of saltsFormation of salts

2) Formation of ester

33)) DecarboxylationDecarboxylation

Q. convert toluene into 1,3,5 trinitrobenzene(TNB(

4) Reduction4) Reduction

5) Conversion of acid5) Conversion of acid--toto--acid chlorideacid chloride

77)) Conversion of acid to amidesConversion of acid to amides

8) Kolb electrolysis

9) Substitution reactions of carboxylic acids9) Substitution reactions of carboxylic acidsIN aliphatic acidIN aliphatic acidHell-Volhard-Zeliniki reactionHell-Volhard-Zeliniki reaction

It occurs in aliphatic acid atIt occurs in aliphatic acid at αα--positionposition

CH3COOH

acetic acid

Cl2

PCl CH2COOH

2-chloroacetic acid

Cl2

PCl C

Cl

COOH

H

Cl2

P

Cl C

Cl

COOH

Cl

2,2-dichloroacetic acid

2,2,2-trichloroacetic acid

Cl2

Pno reaction

Other exampleOther example

مع التفاعل نفس يتم أن Br2يمكن

.1B) Aromatic acid: –COOH is m-directing group.

COOH

Conc. HNO3

Conc. H2SO4

benzoic acid

COOH

NO2

3-nitrobenzoic acid

Cl2

P

Cl2

PH3C C

Cl

COOH

Cl

Cl2

P

2,2-dichloropropanoic acid

no reactionH3C CH2 COOH

propionic acid

H3C CH

COOH

2-chloropropanoic acid

Cl

1010)Hunsdiecker reaction)Hunsdiecker reaction

this is one way of shorting the carbon chain

Derivative of carboxylic acidsDerivative of carboxylic acids (1) Acid halide(1) Acid halide

NomecaltureNomecalture حرف - اسم eباستبدال oyl ب alkaneمن

halide

Alkane alkanoyl halide

باستبدال - الحمض اسم من yl ب icأوchloride

PreparationsPreparations

1-From acids1-From acids

RCOOHPCl5

R C

O

Cl + HCl + POCl3

RCOOHSOCl2

R C

O

Cl + HCl + SO2Thionylchloride

RCOOHPCl3

R C

O

Cl3 + H3PO3

2- From Aldhydes2- From Aldhydes

Chemical reactionsChemical reactions

R C

O

HCl2

R C

O

Cl + HCl

Reaction of acid chloride with R-MgXReaction of acid chloride with R-MgX

(2) Acid anhydride

بكلمة - 9 متبوعا الحمض اسم بذكر تتم anhydrideالتسمية

Preparation

1-From acid chloride1-From acid chloride

(2) From acetylene

(3) From ketene(3) From ketene

Chemical reactionsChemical reactions

(3) (3) AmideAmide

اسم بذكر تتم حرف alkaneالتسمية منه بـ eمحذوفا5 اسم amideواستبداله أو 5 محذوفا الحمض

amide ب واستبدالها oicمنه

Preparation of amidesPreparation of amides

(1) From acid chloride, anhydride, ester

(2) From (2) From nitrilesnitriles

2) Hofmann degradation of amide

Q. Convert acetic acid to methyl amine.

اإلجابة

(1 Hydrolysis

Chemical reactionsChemical reactions

3) Dehydration3) Dehydration

4 ) Action of nitrous acid

(4) (4) EstersEsters

كاآلتى تتم التسميةاسم - 1 `Rذكرمنه - 2 محذوفا5 الحمض اسم اليه ic -ذكر ateومضافا5

PreparationPreparation

Reactions of esters

Reaction with Grignard to form t-alc.

Claisen condensation of esterClaisen condensation of ester

Mechanism