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Delhi

Carboxylic Acids

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Published in: Chemistry
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Carboxylic acids

Shilpi M / Rajkot

4 years of teaching experience

Qualification: M.Sc, MBA

Teaches: Chemistry

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  1. Exam 3 notes LSW Organic Chemistry Carboxylic Acids and Derivatives Carboxylic Acids and Derivatives Nomenclature: O O Structure General Formula Type Suffix Prefix Cyclic On a ring Alkyl substituents R —N R __H O R x CnH2nCOO Carboxylic Acid Alkan-oic acid carboxy- alkane none None CnH2nCOX halo en Acyl halides Alkan-oyl halide halidealka noyl- none Same None CnH2nCOOCO cnH2n Anhydrides Alkan-oic anhydride none Alkan-dioic anh dride Same None 222 CnH2nCOOCm 21114-2 Esters Alkyl alkan —oate alkoxycarbo nyl- carbalkox - lactones cycloalkaneca rboxylate alkyl o R" CnH2nCONR2 Amides Alkan- amide carbamoyl- lactams cycloalkanec arbamide N-alkyl CnH2nCN Nitriles Alka- nitrile Alkan- onitrile cyano- None Same None
  2. Exam 3 notes LSW Structure Simple O HO HO Organic Chemistry Carboxylic Acids and Derivatives CH3CH2C=N H O—CH2CH3 O OH OH Physical Properties: Carboxylic acids H-bonding: Hydrogen bonded dimers: Melting and boiling points: Aqueous solubility: 223
  3. Exam 3 notes LSW Acidit . Compound I-ICI or H2S04 Organic Chemistry Carboxylic Acids and Derivatives pKa Carboxylic acid Phenols Alcohols Adjacent electron withdrawing substituents: Carbox lic Acid Ethanoic acid Pro anoic acid Fluoroethanoic acid Chloroethanoic acid Dichloroethanoic acid Trichloroethanoic acid Nitroethanoic acid 224 Structure CH3C02H CH3CH2C02H CH2FC02H CH2CIC02H CHC12C02H CC13C02H 02NCH2C02H
  4. Exam 3 notes LSW Reactivity: Organic Chemistry Carboxylic Acids and Derivatives As an acid. RCOOH + B-» RCOO- + HB As an electrophile in nucleophilic acyl substitution reactions. RCOOH + Nu -Y RCONu O Nu- + LG As a base when it is a carboxylate. RCOO- + 1-430+ -Y RCOOH + H20 As a Nucleophile when it is a carboxylate. RCOO- RCOOE Resonance interaction of the carbonyl with the Ione pair of the adjacent heteroatom: Observed reactivity order: acyl halides anhydrides aldehydes ketones esters carboxylic acids amides 225
  5. Exam 3 notes LSW Derivative Acyl chloride Anhydride (Aldehyde) (Ketone) Ester Acid Amide Carboxylate Organic Chemistry Carboxylic Acids and Derivatives Substituent Electronic Reaction Leaving Effect Relative Reactivit -a -OC=OR (RC=OH) (RC=OR) -OR -OH -NH2 -O Grou acyl substitution acyl substitution acyl addition acyl addition acyl substitution acyl substitution acyl substitution acyl substitution Mechanism of Nucleophilic acyl addition: O Nu:e Mechanism of Nucleophilic acyl substitution: Nu:e LG 226
  6. Exam 3 notes LSW Activating EDG Refer auce Deactivating —S-OH Organic Chemistry Carboxylic Acids and Derivatives Most Acöaüng I'TI--I.-, OH —öR — öCR —R —C=CR2 —CH —CR O —COR. —COH —ccl —CF.3 —CEN Ill O 3 Strongly Activating Moet-ately Activating ortho f para dire.ting Weak-bf Activating Weakly Deactivating Moderately Deactivating meta diræting Strongly Deactivating Most Deactivating 227
  7. Exam 3 notes LSW RC-=-N Organic Chemistry Carboxylic Acids and Derivatives Pre arations of Carbox lic Acids Carbonation of Grignards Hydrolysis of Nitriles Oxidation of 10 Alcohols Oxidation of Aldehydes Oxidation of Alkyl Benzenes RX RLG Mg RMgX 1. C02 2. H30+ H30+ HEAT RCH20H o RCH ArCHR2 Oxidation Oxidation Oxidation R OH O R OH O R OH O R OH Ar OH Carbonation of Grignard Reagents, RMgX, by C02 Mg RMgX O 1. C02 2. H30+ R OH Reaction usually in Et20 or THF followed by 1-130+ work-up Reaction type: Limitations: Mechanism: RMgBr 228 O R-C-OH
  8. Organic Chemistry Exam 3 notes Carboxylic Acids and Derivatives LSW Hydrolysis of Nitriles RC-=N RLG Reaction type: 1) Nucleophilic 2) Nucleophilic Oxidation of Primary Alcohols O RCH20H RCH Reaction type: Reagents: Oxidation of Alkyl Benzenes CHR2 Reaction type: Reagents : Limitations: 229 H30+ HEAT O R OH R OH C02H
  9. Exam 3 notes LSW Organic Chemistry Carboxylic Acids and Derivatives Reactions of Carboxylic Acids Reaction as an acid O O/ Overall Reaction: O O— Preparation of Carboxylic Acid Derivatives Acyl Chloride RAOH + INERT BASE soc12 O O S02 Acid Anhydride Ester Amide R'JQOH O R OH R OH HEAT ROH RR"NH 230 HEAT + H20 + 1-120 O + H 20
  10. Organic Chemistry Carboxylic Acids and Derivatives O make Froml O O R OR O SOC12 or R OH PC13 (PBr3) O O RGN Exam 3 notes LSW To Heat, -H20 O O ZIL O xo—IL RC02 RCOCI O R'OH R'OH R'OH heat R'OH, heat R'-Br or -1 231 R NR2R O H2 1-12 o o H20, H30+ heat H20, H30+ heat H30+ H20, heat R2NH R2NH R2NH R2NH heat H20, heat H20, H20, HO H20, HO heat H20, HO heat
  11. Exam 3 notes LSW Organic Chemistry Carboxylic Acids and Derivatives Hydride Reduction Reactions Acid Ester Amide Nitrile + LiAlH4 R OH O A + LiAlH4 R OR O + LiAlH4 R NI-12 R-C=N + LiAIH4 Nucleophilic Addition Reactions Freidel Crafts Acylation Ester Alkylation Nucleophilic Addition to Nitriles Alkylation of Nitriles R' O OR" Nu-H 2 RLi or 2 RMgX R' 2 RLi or 2 RMgX 232 2. 1--130+ workup 2. H30+ workup OH + H20 OH + ROH R NI-12 R NH2 R + HCI OH CONTINUES REACTING O R'
  12. Exam 3 notes LSW Organic Chemistry Carboxylic Acids and Derivatives Nucleophilic Acyl Substitution Two Important Steps: Formation of the new o bond to the nucleophile, Nu. Breaking of the o bond to the leaving group, LG. Nu:e LG Nucleophilic Acyl Substitution: Reactive type O Nu:- R LG O Nucleophilic Acyl Substitution: Less Reactive Activating the Nucleophile Activating the Electrophile R LG O HNu: O 233
  13. Exam 3 notes LSW Organic Chemistry Carboxylic Acids and Derivatives Preparation of Acyl Chlorides INERT BASE + SOC12 -...................................................................................> R OH Preparation of Acid Anhydrides O 2 R OH O O HEAT Preparation of Esters O + ROH R OH Preparation of Amides A + RR"NH R OH O HEAT 234 S02 H 20 H 20
  14. Exam 3 notes LSW Organic Chemistry Carboxylic Acids and Derivatives Reduction of Carboxylic Acids O + LiAlH4 R OH OH + 1-120 Reaction usually in Et20 or THF followed by 1-130+ work-ups Reaction type: a-Halogenation (Hell-Volhard-ZeIinsky reaction) PBr3 + Br2 R-CH2 OH Reaction type: Reagents: Regioselectivity: Mechanism: Importance: 235 O R—CH OH

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