Transcript Carboxylic acids R-COOH

Carboxylic acids
R-COOH
Nomenclature
A) IUPAC
.oic acid ‫ ونستبدله بـ‬e ‫ونحذف حرف‬alkane ‫ نأخذ اسم‬alkanoic acid
Alkane
.1 ‫ كرقم‬-COOH ‫مع مراعاة ترقيم‬
‫‪B) Common name‬‬
‫‪ -‬يمكن بدالً من استخدام الترقيم الحروف الالتينية ‪δ ، γ ، β ، α‬‬
Nomeclature of some aromatic acids
Preparation of carboxylic acids
(1) Oxidation of 1ry alcohols or aldehydes
Oxidizing agent may KMnO4, K2Cr2O7
)2( From Grignard reagent
3(Oxidation of alkyl benzene
4) Hydrolysis of nitriles
Nitrile means compounds containing CN
‫‪ -‬هذه الطريقة تصلح لزيادة عدد ذرات أى مركب ذرة كربون واحدة كاآلتى ‪:‬‬
‫‪e.g. convert n-propanol to butanoic acid‬‬
(5)From olefins (alkenes)
)6( From acetylenes
)7( Haloform reaction
Reaction of carboxylic acids
1) Formation of salts
2) Formation of ester
3) Decarboxylation
Q .convert toluene into 1,3,5 trinitrobenzene(TNB(
4) Reduction

5) Conversion of acid-to-acid chloride
7) Conversion of acid to amides
8) Kolb electrolysis
9) Substitution reactions of carboxylic acids
IN aliphatic acid
Hell-Volhard-Zeliniki reaction

It occurs in aliphatic acid at α-position
CH3COOH
Cl2
Cl CH2COOH
P
acetic acid
2-chloroacetic acid
Cl2
P
Cl
Cl C COOH
H
2,2-dichloroacetic acid
Cl
Cl C COOH
Cl
2,2,2-trichloroacetic acid
Cl2
P
no reaction
Cl2
P
Other example
Cl
H3C C COOH
H
Cl2
H3C CH2 COOH
P
propionic acid
Cl
H3C C COOH
Cl
Cl2
P
2-chloropropanoic acid
Cl2
P
no reaction
2,2-dichloropropanoic acid
Br2 ‫يمكن أن يتم نفس التفاعل مع‬
B) Aromatic acid:
COOH
–COOH is m-directing group..1
COOH
Conc. HNO3
Conc. H2SO4
benzoic acid
NO2
3-nitrobenzoic acid
10)Hunsdiecker reaction
this is one way of shorting the carbon chain
Derivative of carboxylic acids
(1) Acid halide

Nomecalture
oyl halide ‫ ب‬alkane ‫ من اسم‬e ‫ باستبدال حرف‬alkanoyl halide
Alkane
yl chloride ‫ ب‬ic ‫ أو من اسم الحمض باستبدال‬-
Preparations
1-From acids
PCl5
O
R C Cl + HCl + POCl3
SOCl2
O
R C Cl + HCl + SO2
RCOOH
RCOOH
Thionyl
chloride
PCl3
3 RCOOH
O
R C Cl + H3PO3
2- From Aldhydes
O
R C H
Cl2
O
R C Cl + HCl
Chemical reactions

Reaction of acid chloride with R-MgX
)2(Acid anhydride
anhydride ‫التسمية تتم بذكر اسم الحمض متبوعا ً بكلمة‬-
Preparation
1-From acid chloride
)2(From acetylene
(3) From ketene
Chemical reactions

‫‪)3(Amide‬‬
‫التسمية تتم بذكر اسم ‪ alkane‬محذوفا ً منه حرف ‪ e‬واستبداله بـ ‪ amide‬أو اسم الحمض محذوفا ً‬
‫منه ‪ oic‬واستبدالها ب ‪amide‬‬
Preparation of amides
)1(From acid chloride, anhydride, ester
(2) From nitriles
Chemical reactions
1(Hydrolysis
2) Hofmann degradation of amide
.Q. Convert acetic acid to methyl amine
‫اإلجابة‬

3) Dehydration
4) Action of nitrous acid
‫‪)4(Esters‬‬
‫التسمية تتم كاآلتى‬
‫‪ -1‬ذكر اسم `‪R‬‬
‫‪ -2‬ذكر اسم الحمض محذوفا ً منه ‪ -ic‬ومضافا ً اليه ‪ate‬‬
Preparation
Reactions of esters
.Reaction with Grignard to form t-alc
Claisen condensation of ester
Mechanism