OH – C – CH 2 – C – CH 2 – C – OH O║O║ O ║ HO – C O║O║ OH

 Carboxylic acids are organic acids characterized by the presence of a CARBOXYL GROUP, which has the formula -C(=O)OH, usually written -COOH or -CO2H.

KMnO 4 K 2 Cr 2 O 7 (O)

CH 3 – CH 2 – OH K 2 Cr 2 O 7 (O) CH 3 – C – H + H 2 O O║O║ (O) CH 3 – C – OH O║O║

H – C – OH O║O║

HO – C – CH 2 – C – OH O║O║ O║O║

HO – C – C – OH O║O║ O║O║

CH 3 – (CH 2 ) 18 – C – OH O║O║

OH – C – CH 2 – C – CH 2 – C – OH OH O ║ HO – C O║O║ O║O║

CH3 – (CH 2 ) 7 – CH=CH – (CH 2 ) 7 – C – OH O║O║

View patricia pen's mapTaken in (See more photos here)more photos here The leaves are such a rich shiny green they begged me to take a picture.

CH 3 – (CH 2 ) 10 – C – OH O║O║

CH 3 – (CH 2 ) 16 – C – OH O║O║

CH 3 – C – OH O║O║

CH 3 – CH – C – OH O║O║ OH

CH 3 – (CH 2 ) 2 – C – OH O║O║

CH 3 – (CH 2 ) 14 – C – OH O║O║

 A carboxylic acid is named in the IUPAC system by replacing the –e of the alkane name by Functional group suffix = -oic acid.  The carboxyl carbon is designated as number # 1, and other substituents are located and named accordingly.  However, common names derived from their natural source are used extensively for most carboxylic acid, and the greek letters alpha, beta, gamma and delta are used to show the location of side groups.

Formula Common Name Source IUPAC Name Melting Point Boiling Point HCO 2 H formic acid ants (L. formica) methanoic acid 8.4 ºC101 ºC CH 3 CO 2 H acetic acid vinegar (L. acetum) ethanoic acid 16.6 ºC118 ºC CH 3 CH 2 CO 2 H propionic acid milk (Gk. protus prion) propanoic acid ºC141 ºC CH 3 (CH 2 ) 2 CO 2 H butyric acid butter (L. butyrum) butanoic acid -5.5 ºC164 ºC CH 3 (CH 2 ) 3 CO 2 H valeric acidvalerian root pentanoic acid ºC186 ºC CH 3 (CH 2 ) 4 CO 2 H caproic acid goats (L. caper) hexanoic acid -4.0 ºC205 ºC CH 3 (CH 2 ) 5 CO 2 H enanthic acid vines (Gk. oenanthe) heptanoic acid -7.5 ºC223 ºC CH 3 (CH 2 ) 6 CO 2 H caprylic acid goats (L. caper) octanoic acid 16.3 ºC239 ºC CH 3 (CH 2 ) 7 CO 2 H pelargonic acid pelargonium (an herb) nonanoic acid 12.0 ºC253 ºC CH 3 (CH 2 ) 8 CO 2 H capric acidgoats (L. caper) decanoic acid 31.0 ºC219 ºC

Give the IUPAC & COMMON name of D’ Given Structure CH 3 – (CH 2 ) 4 – C – OH O║O║

Give the IUPAC & COMMON name of D’ Given Structure CH 3 – (CH 2 ) 2 – C – C – OH O║O║ OH

Give D’ IUPAC name of D’ CARBOXYLIC structure HO – C – CH – C – CH – CH 3 CH 2 – CH 3 NO 2 O║O║ O║O║

Give D’ COMMON name of D’ CARBOXYLIC structure CH 3 – (CH 2 ) 2 – C – CH – C – (CH 2 ) 2 – C – OH NO 2 CH 3 HOO║O║ O║O║

Give D’ IUPAC name of D’ CARBOXYLIC structure CH 3 – (CH 2 ) 2 – C – CH 2 – C – CH 2 – CH 3 CH 2 – CH 3 HO – C – 2 HC (CH 2 ) 2 – CH3 CH 3 – CH 2 O║O║

What if there’s a DOUBLE or TRIPLE bond in a structure? CH 3 – C ≡ C – C – OH O║O║ O ║ C – OH

Give D’ IUPAC name of D’ CARBOXYLIC structure HO – C – CH – CH 2 – C ≡ C – C – CH 3 CH 3 – (CH 2 ) 2 CH 2 – CH 3 O║O║

Give D’ IUPAC name of D’ CARBOXYLIC structure CH 2 O ║ C – OH HO

Give D’ IUPAC name of D’ CARBOXYLIC structure O ║ C – OH CH 3 – (CH 2 ) 4

Give D’ IUPAC name of D’ CARBOXYLIC structure CH3 – CH ═ CH – CH2 – C ≡ C – C – OH O║O║

What if there are MULTIPLE CARBOXY in a structure? OH – C – CH2 – CH2 – C – OH O║O║ O║O║ OH – C – (CH2) 3 – C – OH O║O║ O║O║

Give D’ IUPAC name of D’ CARBOXYLIC structure OH – C – (CH2) 4 – C – OH O║O║ O║O║

Give D’ IUPAC & COMMON name of D’ CARBOXYLIC structure OH – C – CH2 – C – CH2 – C – OH O║O║ O║O║ OH O ║ HO – C

Give D’ IUPAC name of D’ CARBOXYLIC structure O ║ HO – C O ║ HO – C O ║ HO – C 3 HC

What if a CARBOXY group is bound to a benzene structure? O ║ C – OH

Give D’ IUPAC name of D’ CARBOXYLIC structure Cl O ║ C – OH Br

Give D’ IUPAC name of D’ CARBOXYLIC structure O ║ C – OH NO 2

Give D’ IUPAC & COMMON name of D’ CARBOXYLIC structure OH O ║ C – OH

Give D’ IUPAC & COMMON name of D’ CARBOXYLIC structure O ║ C – OH H2NH2N

 Carboxylic acids are POLAR, and form HYDROGEN BONDS with each other.POLARHYDROGEN BONDS  C.A. low MW r LIQUID at room temperature w/ sharp unpleasant ODOR.  HIGH temperatures, in vapor phase  C.A. usually exist as DIMERIC pairs.  LOWER C.A.(1 to 4 carbons) are MISCIBLE with water, whereas HIGHER carboxylic acids are very much less-soluble due to the increasing HYDROPHOBIC nature of the alkyl chain.  They tend to be rather SOLUBLE in less-polar solvents such as ETHERS and ALCOHOLS.

COMMONBOILING °C MELTING °C SOLUBILITY Formic acid1018infinite Acetic acid11817Infinite Propionic acid infinite Butyric acid164- 5infinite Valeric acid Caproic acid Caprylic acid23917insoluble Capric acid27032insoluble Lauric acid29944insoluble Myristic aciddecomposes58insoluble Palmitic aciddecomposes63insoluble Stearic aciddecomposes71insoluble

CLASSCOMPOUND WEIGHTBOILING Alkanepentane7235 °C EtherDiethyl ether 7435 °C Aldehydebutanal7276 °C Alcohol1 - butanol74118 °C Carboxylic acid Propanoic acid °C

REACTION MECHANISM A step by step description of how a chemical reaction occurs.

N EUTRALIZATION A reaction that involves acids and bases. IONIZATION A reaction that deals with cations & anions.

A process of forming an ester. ESTERIFICATION An organic compound. ESTERS

Carboxylic acid + Water ↔ Carboxylate ion + Hydronium ion CH 3 – C – O – H + H 2 O O║O║ CH 3 – C – O ־ + H 3 O + O║O║

O ║ C – O – H + H 2 O O ║ C – O ־ + H 3 O + CH 3 – (CH 2 ) 4 – C – O – H O║O║ + H 2 OCH 3 – (CH 2 ) 4 – C – O ־ O║O║ + H 3 O +

Carboxylic acid + Base → Carboxylate salt + Water CH 3 – C – O – H + K – OH O║O║ CH 3 – C – O ־ K + + H2O O║O║

CH 3 – (CH 2 ) 3 – C – O – H O║O║ + Li – OH O ║ C – O – H + Na – OH O ║ C – O ־ Na + + H 2 O CH 3 – (CH 2 ) 3 – C – O ־ Li + + H 2 O O║O║

Carboxylic acid + Alcohol → ESTER + Water H+/ heat CH 3 – C – OH + H – O – CH 3 O║O║ H+/ heat CH 3 – C – O – CH 3 + H 2 O O║O║

CH 3 – (CH 2 ) 2 – C – OH O║O║ + H – O – CH 2 – CH 3 H+/ heat CH 3 – (CH 2 ) 2 – C – O – CH 2 – CH 3 O║O║ + H 2 O

O ║ C – OH OH + H – O – CH 3 H+/ heat O ║ C – O – CH 3 OH + H 2 O

Do a sequence of reaction to produce methyl butyrate an apple flavor, used in food & cosmetic industry. CH 3 – (CH 2 ) 2 – C – OH O║O║ + H – O – CH 3 H+/ heat CH 3 – (CH 2 ) 2 – C – O – CH 3 O║O║ + H 2 O

Do a sequence of reaction to dissociate ENANTHIC ACID. CH 3 – (CH 2 ) 5 – C – O – H O║O║ + H 2 OCH 3 – (CH 2 ) 5 – C – O ־ O║O║ + H 3 O +

Do a sequence of reaction to produce Calcium propanoate a carboxylic acid salt, used commercially as preservative in bread, cakes & cheese. CH 3 – CH 2 – C – O – H O║O║ + Ca – OH CH 3 – CH 2 – C – O ־ Ca + O║O║ + H 2 O

Do a sequence of reaction to produce octyl acetate an orange flavor, used in food & pharmaceutical industry. CH 3 – C – OH O║O║ + H – O – (CH 2 ) 7 – CH 3 H+/ heat CH 3 – C – O – (CH 2 ) 7 – CH 3 O║O║ + H 2 O

Do a sequence of reaction to dissociate DECANOIC ACID. CH 3 – (CH 2 ) 8 – C – O – H O║O║ + H 2 OCH 3 – (CH 2 ) 8 – C – O ־ O║O║ + H 3 O +

Do a sequence of reaction to produce Sodium Stearate a long chain carboxylic acid salt, used commercially as Surfactant for Soaps. CH 3 – (CH 2 ) 16 – C – O – H O║O║ + Na – OH CH 3 – (CH 2 ) 16 – C – O – Na O║O║ + H 2 O

 What are organic compound ESTERS?  Give some examples of ESTERS?  Cite some industrial applications of ESTERS.  References: All organic chemistry book will do.