DERIVATIVES OF CARBOXYLIC ACIDS

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1 13 Rl RH RNH 2 RR RR DERIVATIVES F ARBXYLI AIDS HAPTER SUMMARY 13.1 Structure and Nomenclature of arboxylic Acid Derivatives A. Structure arboxylic acids and their derivatives can be expressed as variations of a single formula in which an electronegative atom - oxygen, nitrogen, or halogen - is attached to a carbon-oxygen double bond. The fundamental acid derivatives and their electronegative groups are acid chlorides, l; acid anhydrides, 2 R; carboxylic acids, H; esters, R; and amides, NH 2, NHR, or NR 2. Acid chlorides and 290

2 Derivatives of arboxylic Acids hapter 13 anhydrides are very reactive and are used in synthetic organic chemistry; the others are found abundantly in nature. The reactivity of carboxylic acids and their derivatives is a result of polar bonds, non-bonding electron pairs and the carbonoxygen double bond. The = can attract both nucleophiles and electrophiles. B. Nomenclature of arboxylic Acid Derivatives arboxylic acids are named by adding the suffix oic acid to the base name. Acid chlorides are name by changing the ic acid of the parent carboxylic acid to yl chloride. The suffix acid is changed to anhydride to name acid anhydrides. Esters are named like acid salts by changing ic acid to ate and preceding the name by the name of the alkyl group. To name amides, the oic acid is changed to amide. NNETINS 13.1 Aspirin and ther Analgesics 13.2 Nucleophilic Acyl Substitution Reactions A. The Reaction A characteristic reaction of carboxylic acid derivatives is nucleophilic acyl substitution. In this reaction a negative or neutral nucleophile replaces a leaving group to form a substitution product. The leaving groups and nucleophiles are the groups that define the various acid derivatives; as a result, the reaction usually involves the conversion of one acid derivative into another. The order of reactivity of acid derivatives is acid chloride > anhydride > acid or ester > amide. In general, reaction of any of these derivatives with water produces acids; with alcohols, esters result; and with amines, amides are formed. B. The Reaction Mechanism Nucleophilic acyl substitution can be initiated by a negative or neutral nucleophile attacking the partially positive carbonyl carbon. In this two-step mechanism, a tetrahedral intermediate is formed; loss of the leaving group produces the new acid derivative. Alternatively, 291

3 hapter 13 Derivatives of arboxylic Acids the reaction can be acid catalyzed. In this mechanism, a hydrogen ion bonds to the carbonyl oxygen to form a carbocation. The nucleophile bonds to the carbocation to form the tetrahedral intermediate; when the leaving group departs the new acid derivative is formed Nucleophilic Acyl Substitution Reactions of Acid hlorides A. Synthesis of Acid hlorides arboxylic acid chlorides are synthesized by treating a carboxylic acid with thionyl chloride. B. Reactions of Acid hlorides Acid chlorides react with sodium salts of carboxylic acids to form anhydrides, with alcohols to form esters, with water to form acids, and with amines to form amides.. Nucleophilic Acyl Substitution Mechanism These reactions generally proceed by a nucleophile initiated mechanism. An acid salt, water, alcohol, ammonia, or amine attacks to form a tetrahedral intermediate. The new derivative is formed upon departure of the chloride (as Hl) Nucleophilic Acyl Substitution Reactions of Acid Anhydrides A. Synthesis of Acid Anhydrides Acid anhydrides are synthesized from acid chlorides and carboxylic acid salts. B. Reactions of Acid Anhydrides Anhydrides react with alcohols to form esters, with water to form carboxylic acids, and with amines to form amides.. Nucleophilic Acyl Substitution Mechanism The reaction mechanism is usually nucleophile initiated. A Lewis base - alcohol, water, ammonia, or amine - attacks the carbonyl carbon to 292

4 Derivatives of arboxylic Acids hapter 13 form a tetrahedral intermediate. Elimination of a molecule of carboxylic acid produces the new acid derivative Nucleophilic Substitution Reactions of arboxylic Acids A. Reactions of arboxylic Acids arboxylic acids react with thionyl chloride to form acid chlorides. Reaction with alcohols gives esters, and with amines, amides are formed. B. Nucleophilic Acyl Substitution Mechanism Many nucleophilic acyl substitution reactions of carboxylic acids are acid-initiated. For example, in esterification, the carbonyl group is protonated, alcohol attacks to form the tetrahedral intermediate, proton transfers occur, and water leaves Nucleophilic Acyl Substitution Reactions of Esters A. Reactions of Esters Esters can be converted to acids with water; reaction with an alcohol produces a new ester by a process called transesterification. Esters react with amines to form amides. B. Nucleophilic Acyl Substitution Mechanism Esters react by both acid and nucleophile initiated mechanisms. Hydrolysis of esters by acid catalysis is exactly the reverse of the mechanism for the acid-catalyzed esterification of a carboxylic acid. Base-catalyzed hydrolysis of esters is called saponification. Hydroxide attacks to form a tetrahedral intermediate. Loss of alkoxide ion then occurs. The alkoxide neutralizes the resulting carboxylic acid to form the salt.. Synthesis of Esters by Nucleophilic Acyl Substitution To determine the materials for ester synthesis, look at the carbon oxygen double bond. n one side is a single bond to an oxygen. Mentally break this bond and put a hydrogen on the oxygen; this is the 293

5 hapter 13 Derivatives of arboxylic Acids alcohol to use. n the carbonyl carbon place an H, l, or 2 R to determine the acid or acid derivative to use in the ester synthesis Nucleophilic Acyl Substitution Reactions of Amides Amides are the least reactive of the carboxylic acid derivatives; they can be prepared from any of the other acid derivatives. Hydrolysis, either acid- or base-catalyzed, to form acids is the only nucleophilic acyl substitution reaction Polyamides and Polyesters Polyamides such as Nylon are formed from dicarboxylic acids and diamines. Polyesters such as Dacron are formed from the reaction of dicarboxylic acids or diesters with dialcohols Nucleophilic Addition Reactions of arboxylic Acid Derivatives A. Reduction with Lithium Aluminum Hydride arboxylic acid derivatives can also undergo nucleophilic addition reactions. By a combination of nucleophilic acyl substitution and nucleophilic addition, all of the acid derivatives except amides can be reduced to primary alcohols using lithium aluminum hydride. The first hydride ion displaces the leaving group; the resulting aldehyde is reduced to the primary alcohol. Reduction of amides produces amines. B. Reaction with Grignard Reagents Esters and acid chlorides react with Grignard reagents to form tertiary alcohols. The first mole of Grignard displaces the alkoxide or chloride leaving group to form a ketone. The ketone undergoes nucleophilic addition to form the tertiary alcohol Reactions of Acid Derivatives Involving arbanions A. Malonic Ester Synthesis ertain acid derivatives are capable of reactions involving intermediate carbanions. The malonic ester synthesis is used to synthesize substituted acetic acids. The reaction involves abstraction of 294

6 Derivatives of arboxylic Acids hapter 13 alpha hydrogens to form resonance stablized carbanions; these carbanions become the nucleophiles in reactions with alkyl halides. B. laisen ondensation The laisen condensation is a carbanion reaction in which the carbanion produced by alpha hydrogen abstraction on an ester displaces the alkoxy group of another ester molecule; the reaction produces keto esters. NNETINS 13.2 Barbiturates SLUTINS T PRBLEMS 13.1 Structures of Acid Derivatives (a) H 3 H 2 H 2 2 H H 3 H 2 2 H 3 H 3 2 H 2 H 3 H 2 H 2 H 2 H 3 H 3 H 3 H 3 H 2 H H 2 HH 3 (b) H 3 H 2 NH 2 H 3 NHH 3 HNHH 2 H 3 HN(H 3 ) 2 (c) H 3 H 2 H 2 l (H 3 ) 2 Hl (d) H 3 H 3 H 3 H 2 H 2 H 3 H 3 H 2 H Nomenclature of Acid hlorides (a) pentanoyl chloride; (b) 2-propenoyl chloride; (c) p-nitrobenzoyl chloride 13.3 Nomenclature of Acid Anhydrides (a) ethanoic anhydride; (b) pentanoic anhydride; (c) ethanoic pentanoic anhydride 295

7 hapter 13 Derivatives of arboxylic Acids 13.4 Nomenclature of Esters (a) methyl ethanoate; (b) ethyl 2-propenoate; (c) isopropyl m-chlorobenzoate 13.5 Nomenclature of Amides (a) ethanamide; (b) 2-propenamide; (c) p-bromo-n-methylbenzamide; (d) N-methylethanamide; (e) N,N-dimethyl-2-propenamide; (f) p-bromo-n-ethyl-n-methylbenzamide 13.6 Synthesis of Acid hlorides Sl 2 l + S 2 + Hl 13.7 Reactions of Acid hlorides H 3 l + Reagents a-f + Hl (Nal in c) a) H 3 H b) H 3 H 2 H 3 c) H 3 H 3 d) H 3 NH 2 e) H 3 NHH 3 f) H 3 N(H 2 H 3 ) Nucleophilic Acyl Substitution Mechanism.. H 3 l.... _ H 2 - Hl H 3 l H3 + H 2.. tetrahedral intermediate H 13.9 Synthesis of Acid Anhydrides H 3 l + H 3 H 2 Na H 3 H 2 H 3 + Hl H 3 Na + H 3 H 2 l H 3 H 2 H 3 + Hl 296

8 Derivatives of arboxylic Acids hapter Reactions of Acid Anhydrides H 3 H 3 + Reagents a-d + H 3 H a) H 3 H b) H 3 H 2 H 3 c) H 3 NH 2 d) H 3 NHH Nucleophilic Acyl Substitution Mechanism - NH - H 3 3 H H 3 H 3 H 3 H 3 neutral tetrahedral nucleophile + NH 3 intermediate H 3 NH Reactions of arboxylic Acids H 3 H 2 reagents a-d + H 2 (S 2 + Hl in part a) (a) H 3 H 2 l (b) H 3 H 2 H 3 (c) H 3 H 2 NH 2 (d) H 3 H 2 NHH Preparations of Amines from arboxylic Acids 2 H and (H 3 ) 2 NH Acid atalyzed Esterification Mechanism The Reaction H 3 H H 3 + H 2 The Mechanism H H H + H 3 H H H H 3 tetrahedral intermediate 297

9 hapter 13 Derivatives of arboxylic Acids H H H+ - H 2 - H + H 3 H 3 H Reactions of Esters H 3 H 2 H 3 + Reagents a-d + H 3 H 2 H a) H 3 H b) H 3 H 3 c) H 3 NH 2 d) H 3 N(H 2 H 3 ) Acid and Base atalyzed Ester Hydrolysis The Reaction H 3 + H 2 H 3 H (a) Acid atalyzed Hydrolysis Note that this mechanism is the opposite of the esterification shown in problem Both processes are equilibriums. H - H 3 + H 3 -H H 2 H tetrahedral H 3 intermediate H H H 3 H 3 H H H + + H H (b) Base atalyzed Hydrolysis Saponification H 3 H - H H 3 tetrahedral intermediate H + H 3 + H 3 H 298

10 Derivatives of arboxylic Acids hapter Synthesis of Esters (a) H 3 H 2 H 3 H 2 H (b) Br H + H 3 H 2 H 2 H Hydrolysis of Amides H 3 NH 4 + H 3 NH 2 + H 2 H - H NH Preparations of Amides H 3 H 3 H 3 H 2 l + HNH 3 H 3 H 2 -NH 3 + Hl H 3 H 3 H 3 H 2 H 2 H 3 + HNH 3 H 3 H 2 -NH 3 + H 3 H 2 H H 3 H 3 H 3 H 2 H 3 + HNH 3 H 3 H 2 -NH 3 + H 3 H Polyamides H 2 N NH 2 l l Polyesters H 2 H 2 n Reduction of Acid hlorides with Lithium Aluminum Hydride Following is the equation for reduction of an acid chloride. LiAlH H 2 l 4 H 2 / H 2 H 2 Hl Lithium aluminum hydride will reduce the following acid anhydride and carboxylic acid to the same alcohol product. 299

11 hapter 13 Derivatives of arboxylic Acids H 2 H 2 H 2 H LiAlH 4 Reduction of Amides to Amines (a) H 3 H 2 NH 2 (b) H 3 H 2 H 2 H 2 NHH 3 (c) H 2 N(H 2 H 3 ) Reaction of Grignard Reagents with Esters H 3 H 3 final product H H 3 MgBr H 3 H 3 H 3 H 3 - tetrahedral intermediate ketone H 2 / H 3 tetrahedral intermediate MgBr Malonic Ester Synthesis Et H 2 Et NaEt H 3 (H 2 ) 3 Br 2 +H 3 (H 2 ) 3 H 2 H laisen ondensation Et H(H 2 ) 3 H 3 Et heat H H(H 2 ) 3 H 3 H H 2 H - H 3 H 2 HH 2 H 3 H Nomenclature of arboxylic Acids Section 12.2 (a) butanoic acid; (b) 7-methyloctanoic acid; (c) 2-pentenoic acid; 300

12 Derivatives of arboxylic Acids hapter 13 (d) 4-oxopentanoic acid; (e) 2-aminoethanoic acid; (f) 6-hydroxy-2,4- heptadienoic acid; (g) m-bromobenzoic acid; (h) cyclopentanecarboxylic acid; (i) 1,6-hexandioic acid Nomenclature of Acid hlorides Section 13.1B.1 (a) butanoyl chloride; (b) 2-butenoyl chloride; (c) 3-oxopentanoyl chloride; (d) p-chlorobenzoyl chloride Nomenclature of Acid Anhydrides Section 13.1B.2 (a) butanoic anhydride; (b) propanoic anhydride; (c) butanoic propanoic anhydride Nomenclature of Esters Section 13.1B.3 (a) methyl pentanoate; (b) ethyl butanoate; (c) propyl propanoate; (d) butyl ethanoate; (e) pentyl methanoate; (f) isopropyl propanoate; (g) methyl p-nitrobenzoate; (h) butyl 2,4-hexadienoate Nomenclature of Amides Section 13.1B.4 (a) pentanamide; (b) N-methylbutanamide; (c) N-ethylpropanamide; (d) N,N-dimethylpropanamide; (e) N-ethyl-N-methylethanamide; (f) N,N-diethyl-o-methylbenzamide; (g) 4-hyroxy-N-propyl-2-pentenamide Nomenclature of arboxylic Acid Derivatives Section 13.1 (a) H 3 H 2 H 2 2 H (b) (d) H 3 H 2 H 2 H 2 H 2 H 2 H 2 H 3 (f) NH 2 H (g) HN(H 3 ) 2 (h) H 3 (i) H 3 (H 2 ) 2 (H 2 ) 4 H 3 H 2 N 2 H (c) H 2 N H 2 H 3 (e) H 3 H=H-H=H 2 K N(H 2 H 3 ) 2 (j) H 3 (H 2 ) 2 (H 2 ) 2 H Reactions of Acid Derivatives Section (a) H 3 H 2 l + H 2 H 3 H 2 H (k) l + Hl l 301

13 hapter 13 Derivatives of arboxylic Acids (b) (c) (d) H 3 H 2 H 2 H 3 H 3 H 2 H 3 + H 2 + H 2 H 3 H 2 H + H 3 H 2 H 3 H 2 NH 2 + H 2 3 H 2 H Reactions of Acid hlorides Section 13.3 H 3 H 2 H H 3 H NH 3 The by-product in all of these reactions is Hl except in (a) where it is Nal. (a) H 2 H 3 (b) H (c) H 3 (d) NH 2 (e) NHH 3 (f) NH 2 H Reactions of Acid Anhydrides Section 13.4 The by-product of each of these reactions is H 3 H 2 2 H. H 3 (a) H 3 H 2 H (b) H 3 H 2 HH 3 H 3 (c) H 3 H 2 NH 2 (d) H 3 H 2 N Reactions of arboxylic Acids The by-product of these reactions is water except in (d) where it is S 2 + Hl. (a) H 2 H 2 H 3 (b) NH 2 (c) N(H 3 ) 2 (d) l Reactions of Esters Section 13.6 The by-product of all of these reactions is methanol, H 3 H. (a) H 3 H 2 H (b) H 3 H 2 NH 2 302

14 Derivatives of arboxylic Acids hapter 13 (c) H 3 H 2 NHH 3 (d) H 3 H 2 (H 2 ) 4 H Reactions of Amides Section 13.7 Products (a) are shown NH 3 (b) H 3 H 2 H 3 NHH Preparations of Amides Section 13.7 To make the amide in 13.38a treat any of the following compounds with NH 3. (a) l (b) (c) H (d) H 3 To make the amide in 13.38b treat any of the following compounds with (H 3 ) 2 NH. (a) H 3 H 2 l (b) H 3 H 2 H 2 H 3 (c) H 3 H 2 H (d) H 3 H 2 H Preparations of Esters Section 13.6 To prepare the ester in problem 13.37, treat any of the following compounds with methanol, H 3 H, or with methanol and acid catalyst in (c). (a) H 3 H 2 l (b) H 3 H 2 H 2 H 3 (c) H 3 H 2 H Preparations of Esters Section 13.6 (a) H 3 H 2 H 2 H 2 2 H 3 H (b) H 3 H 2 H 2 2 H 3 H 2 H (c) H 3 H 2 2 H 3 H 2 H 2 H (d) H 3 2 H 3 H 2 H 2 H 2 H (e) H 2 H 3 H 2 H 2 H 2 H 2 H (f) H 3 H 2 2 (H 3 ) 2 HH (g) 2 N 2 H + H 3 H (h) H 3 H=H-H=H 2 H 3 H 2 H 2 H 2 H 303

15 hapter 13 Derivatives of arboxylic Acids Lactones Section 13.6 H 2 H 2 H 2 H H elimination of water here + H Reactions of Diacids Section 13.4 H Heat H 3 H H 3 + H Nucleophilic Acyl Substitution Mechanisms Sections (a) Neutral Nucleophile Initiated _ H 3 H H 3 l H3 l H 3 - Hl H 3 H 3 (b) Neutral Nucleophile Initiated _ H 3 H 2 H - H 3 2 H H H H 3 H 2 H 3 --H H 3 H 3 H 2 H (c) Neutral Nucleophile Initiated _ NH 3 - H H 3 -H 3 H 3 -H 3 H 3 H 3 -NH 2 + NH 3 304

16 Derivatives of arboxylic Acids hapter 13 (d) Negative Nucleophile Initiated Saponification _ - H H 3 H 3 H H - + H H 3 H (e) Acid atalyzed Esterification H 3 H 2 -H H H 3 H 2 H + H 3 H 2 H H H 3 H 2 H H 2 H 3 H H H 3 H H -H 2-2 H 3 H 2 + H 3 H 2 H 2 H 3 H 2 H 3 H 2 H 3 (f) Negative Nucleophile Initiated _ H - - NH 3 -NH 2 -NH 2 H - _ Reactions with LiAlH 4 Section 13.9A (a) H 2 H (b) HH 2 H 2 H (c) H 3 (H 2 ) 12 H 2 H (d) H 3 H 2 H 2 H 2 H 2 NH 2 (e) H 3 H 2 N(H 3 ) Acid Derivatives and Grignard Reagents Section 13.9B H H H H 2 H 3 (a) H 3 H 2 H 2 H 2 H 3 (b) l (c) HH 2 H 2 H Nucleophilic Addition Mechanisms Section

17 hapter 13 Derivatives of arboxylic Acids (a) This mechanism shows the reaction of hydride as a negative nucleophile but does not show the coordination of intermediates with aluminum. H H - - H 3 - H - H 3 -H 3 H 3 -H 3 H 3 H H 3 H H 2 H 3 H H H H (b) As with the previous mechanism, this one involves nucleophilic acyl substitution and nucleophilic addition. MgBr H - H 3-3 MgBr H 3 -H 3 H 3 -H 3 H 3 H 3 H H 3 H 3 Br H 3 H 2 MgBr H 3 H 3 H 3 MgBr H 3 H Grignard Synthesis of Alcohols Section 13.9B H H MgBr 2 (a) H 3 H 2 H 2 H H 3 H 2 H 2 (b) H 2 H 2 H 3 H 3 H 2 H 2 H 2 Br Mg + H 3 H 2 H 2 H 2 MgBr Hydrolysis of Urea Section 13.7 Mg H H 2 H 2 H 2 H 2 H 2 H 2 H 3 H 2 H 2 H 2 H 3 Urea is an amide (actually a diamide) and is subject to hydrolysis by water, the "solvent" in urine. Water is the nucleophile in the substitution and the result can be visualized as carbonic acid and ammonia. The carbonic acid is unstable and decomposes to carbon dioxide. H 2 N NH H NH 3 306

18 Derivatives of arboxylic Acids hapter Decomposition of Aspirin Section 13.6 Aspirin is an ester. In the presence of moisture, such as a humid climate, under prolonged conditions, it can hydrolyze by nucleophilic acyl substitution to an acid and alcohol. The acid formed is acetic acid, vinegar acid. H 3 H 2 H + H 2 2 H + H 3 2 H acetic acid Hydrolysis of Salol Section 13.6 H H H + H 2 + H Hydrolysis occurs here; Salol is an ester. H Na NaH Phenol the basic environment of the small intestine converts salicylic acid to the salt, sodium salicylate ondensation Polymers Section 13.8 a) nylon 6-10 H H N(H 2 ) 6 N (H 2 ) 8 n b) nylon 4-6 H H N(H 2 ) 4 N (H 2 ) 4 n c) polycarbonates H 3 H 3 n Polyurethanes Section 13.8 These polymers appear to be structurally both polyamides and polyesters. 307

19 hapter 13 Derivatives of arboxylic Acids Malonic Ester Synthesis Section 13.10A 2 Et 2 Et 2 H a) NaEt H H 3 H 2 Br H 2 H 3 H H 2 2 H H - H 3 H 2 2 Et 2 Et 2 H heat H 3 H 2 H b) 2 Et NaEt H 2 H 3 H 2 l 2 Et H NaEt 3 H 2 H H 3 Br 2 Et 2 Et 2 Et H 3 H 2 H 3 2 Et H 2 H - 2 H H 3 H 2 H 3 2 H heat H H 3 H 2 H 2 H Familiar Esters Sections 13.1B.3 and 13.6 Pineapple ethyl butanoate H 3 H 2 H 2 HH 2 H 3 H 3 H 2 H 2 H 2 H 3 + H 2 Banana 3-methylbutyl ethanoate H 3 H 3 H 3 HH 2 H 2 HH 3 H 3 H 2 H 2 HH 3 + H 2 range octyl ethanoate H 3 HH 2 (H 2 ) 6 H 3 H 3 H 2 (H 2 ) 6 H 3 Wintergreen methyl o-hydroxybenzoate H H H 3 H H3 + H 2 + H 2 Apricot pentyl butanoate H 3 H 2 H 2 H + H(H 2 ) 4 H 3 Rum ethyl methanoate H HH 2 H 3 HH 2 H 3 H 3 H 2 H 2 (H 2 ) 4 H 3 + H 2 + H 2 308

20 Derivatives of arboxylic Acids hapter laisen ondensation Section 13.10B H 3 H 3 H 3 - H 3 H 2 H 3 H 3 H 3.. _ H 2 H 3 - H 3 H 3 H 2 H H laisen ondensation Section 13.10B a) NaH 3 2 H 3 H 3 H 3 H 2 H 3 + H 3 H b) NaH 2 H 3 3 H 2 H 3 H 3 H 2 HH 3 + H 3 H H 3 NaH c) H 3 + H 3 H 3 3 H 2 H 3 + H 3 H Proteins Proline Phenylalanine Glycine H 2 H H H H NH H H H NH 2 H H 2 H 2 NH H 2 H 2 HNHHNHH 2 H H 2 H 2 NH H 2 309

21 hapter 13 Derivatives of arboxylic Acids Preparation of Medicinal ompounds hapters 12 and 13 H 2 H H 2 Na a) + Na H 2 b) H 3 H 2 NH 2 + H 3 H 3 H 3 2 H 3 H 2 NHH 3 c) H NH 2 + H 3 H 3 H NHH 3 + H 3 2 H d) H 2 N H 3 H 2 H H+ H 2 N H 2 H 3 + H 2 H H H H3 e) + H 3 H H+ + H 2 H H f) + NH heat 3 H NH2 + H 2 2 H H 2 H H 3 g) + H 3 H 3 + H 3 2 H h) H 3 H 2 Et Et H HN HN H H 3 H 2 NH NH 310

22 Derivatives of arboxylic Acids hapter Reaction Mechanisms Section 13.6B H + H 3 18 H 18 H 3 + H 2 In the starting materials, the methanol has the labeled oxygen. Since the ester oxygen has the labeled oxygen in the ester product, the oxygen of the ester must have come from the alcohol. ATIVITIES WITH MLEULAR MDELS 1. Make molecular models of the simplest acid, ester, amide, and acid chloride with only two carbons. 2. Make models of the four esters with the formula 4 H

23 hapter 13 Derivatives of arboxylic Acids 3. Make models of the four amides with the formula 3 H 7 N. 4. Make models of the two acid chlorides with the formula 4 H 7 l.. 312

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