Chapter 16 and GHW#6 Questions Carboxylic Acids, Esters, and Other Acid Derivatives

Bonding Characteristics of Carboxylic Acids A carboxylic acid has functional a carboxyl group. A carboxyl group is a carbonyl group (C=O) with a hydroxo group (—OH) bonded to the carboxyl carbon atom.

Physical Properties of Carboxylic Acids Both polar molecules and hydrogen bonding makes: BP and MP are higher than alcohols, hydrocarbons and ether with comparable carbon numbers

Physical Properties of carboxylic acids derivatives Esters, amides, acid chlorides and acid anhydride have lower boiling and melting points than parent acid, Except Carboxylic Acid Salts

IUPAC Nomenclature of Carboxylic Acid and Esters The IUPAC system deals with functional groups two different ways. Modification of the hydrocarbon name to indicate the presence of a functional group. Acid – R-COOH use -oic ending. Esters –R-COOR’ use -oate ending.

Common Names of Carboxylic Acids

IUPAC Nomenclature of Carboxylic Acid and Esters

Common/IUPAC Nomenclature of Esters

1. Identify the carboxylic acids, esters, amides and acid from the following and give their common and/or IUPAC names. Carboxylic Acids, Esters, and Other Acid Derivatives a)Type:_____________ Name:______________ ____ b) Type:___________________ Name:__________________ c)Type:___________________ Name:__________________ d)Type:____________ Name:______________ e) Type:___________________ Name:__________________ f) Type:___________________ Name:__________________

1. Identify the carboxylic acids, esters, amides and acid from the following and give their common and/or IUPAC names. Carboxylic Acids, Esters, and Other Acid Derivatives g) Type:___________________ Name:__________________ h) Type:___________________ Name:__________________ i) Type:___________________ Name:__________________

2. Draw the condensed formula of following carboxylic acid and their derivatives. a) methyl propanoate b) ethyl pentanoate c) propanoyl chloride d) N-methyl propanamide e) N,N-dimethyl ethanamide f) 2-methyl pentanamide g) 2(  )- aminopropan oic h) butanoic ethanoic anhydride

Polyfunctional Carboxylic Acids Dicarboxylic acids Oxylic acid Oh my, such great apple pie!" (oxalic, malonic, succinic, glutaric, adipic, pimelic) "Metabolic" Acids Propionic acid, (C3 mono acids): lactic, glyceric, and pyruvic acids Succinic acid (C4 diacid): fumaric, oxaloacetic, and malic acids Glutaric acid (C5 diacid):  -ketoglutaric and citric acids

3. Identify type and give name of each of the following poly functional carboxylic acids. a) Type:___________________ Name:__________________ b) Type:________________ Name:_______________ c) Type:__________________ Name:_________________ _ d) Type:___________________ Name:__________________ e) Type:__________ Name:________ f) Type:______________ Name:_____________

3. Give common/IUPAC names of following dicarboxylic acids. Use "Oh my, such great apple pie!" (oxalic, malonic, succinic, glutaric, adipic, pimelic). a) Common:______________ IUPAC:_______________ b) Common:_____________ IUPAC:_______________ c) Common:_____________ IUPAC:_______________ d) Common:_____________ IUPAC:_______________ e) Common:___________ IUPAC:_____________

3. Give common/IUPAC names of following dicarboxylic acids. f) Name:______________g) Name:___________h)Common:___________ IUPAC:_______________

Saturated Fatty Acids Saturated Fatty Acids Long chain even carbon atoms C >10

Unsaturated Fatty Acids Unsaturated Fatty Acids Long chain even carbon atoms with C=C bonds

5. Give type/name of following fatty acids, and their derivatives. a)CH 3 (CH 2 ) 10 CO 2 H Type:________________ Name:_______________ b) CH 3 (CH 2 ) 14 CO 2 H Type:________________ Name:_______________ c) CH 3 (CH 2 ) 16 CO 2 H Type:________________ Name:_______________

5. Give type/name of following fatty acids, and their derivatives. d) H 3 (CH 2 ) 7 CH=CH(CH 2 ) 7 CO 2 H Type:________________ Name:_______________ e) f) Type:________________ Type:____________________ Name:_______________ Name:___________________

Triglycerides: Triesters of glycerol

Preparation of Carboxylic Acids Oxidation of primary alcohol to carboxylic acid (described in reactions of alcohols) Oxidation using Tollen’s basic Ag(NH 3 ) 2 + or Bendict’s CuSO 4 /Na 2 CO 2 /Citrate (described in reactions of aldehydes) Oxidation of alkyl side chain of substituted aromatic hydrocarbons (reactions of aromatic alkyl compounds) Hydrolysis of esters. Described in this chaper) Hydrolysis of acid, amides and cholrides etc.. )

Chemical Reactions of Carboxylic Acids Reaction with strong bases to form acid salts (described below in preparation of acid salts) Reaction with strong alcohols to form esters (described below in preparation of esters) Reaction with halogen compounds to form acid chlorides(described below in preparation of acid chloride preparations) Reaction with ammonia and amine compounds to form amides (described in amides chapter 18) Reduction to alcohols with reducing agents (LiAlH 4, NaBH 4 etc.)

5) Name and complete following reactions a) b) c) d)

5) Name and complete following reactions e) f)

7) Name and complete following reactions. a)Condensation Polymerization b) Aspirin synthesis

7) Name and complete following reactions. c) Cyclic ester formation d) Decarboxylation of  - ketoacids

7) Name and complete following reactions. e) Base hydrolysis of esters f) Base hydrolysis of triglycerides

Base hydrolysis of triglycerides Saponification-Soap formation