VIII Functional Groups 2
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1 VIII Functional Groups Carboxylic Acids Carboxylic Acid: Functional group in which OH is attached to carbon-oxygen double bond Representations of Carboxylic Acids: Functional Groups in Carboxylic Acids: 1
2 8.1.1 Nomenclature a) Common Names: B) IUPAC Names: The suffix for carboxylic acids is -oic Priority: carboxylic acid aldehyde ketone 2
3 General Procedure for Naming Organic Compounds: 1) Name the longest carbon chain containing the highest priority functional group 2) Name the chain based on its single, double, or triple bonds 3) Name the highest priority group with its suffix and other groups with prefixes 4) Number the carbon chain 5) Name and number all other functional groups Physical Properties Carboxylic acids can build hydrogen bonds: They can build very stable dimers: Dimers: Two structural units Carboxylic acids have relatively high boiling points Low molecular weight carboxylic acids are water-soluble 3
4 8.1.3 Acidity Like phenols, carboxylic acids are neutralized by NaOH: The pk a 's of carboxylic acids are around 5 (lower than phenols and alcohols) Example: Reason for high stability is a very polar bond and a very stable anion: Structural Effects: Electron donating group intensifies the negative charge less acidic Electron withdrawing groups remove negative charge more acidic Strength or EWG: 4
5 Number of EWG: Proximity of EWG: Aromatic carboxylic acids EWG enhance acidity (most potent in ortho and para) Nomenclature of the Salts of Carboxylic Acids: Salt: Ionic compound composed of cation from a base and anion from neutralized acid In inorganic acids the suffix -ic acid is changed to ate and prefixing the name with the name of the cation that replaces the acidic hydrogen 5
6 Salts of carboxylic acids are named the same way Synthesis of Carboxylic Acids A) Oxidations of Alkylbenzenes: B) Oxidations of Primary Alcohols: C) Hydrolysis of Nitriles: 6
7 D) Carbonation of Grignard Reagents: General Formula: 8.2 Derivatives of Carboxylic Acid Acyl Group: Carboxylic Acid: Functional group in which OH, hydroxy, is attached to an acyl group Ester: Functional group in which OR, alkoxy, is attached to an acyl group Amide: Functional group in which NH 2, NHR, or NR 2, is attached to an acyl group Acid Chloride: Functional group in which Cl, chloride, is attached to an acyl group Acid Anhydride: Functional group in which RCO 2 of one acid molecule is bonded to the acyl group of another 7
8 8.2.1 Nomenclature of Carboxylic Acid Derivatives Named by changing the suffix A) Acid Chlorides: B) Acid Anhydrides: 8
9 C) Esters: D) Amides: Nucleophilic Acyl Substitution Reactions Nucleophilic Acyl Substitution: group attached to an acyl group, RC=O, is replaced Nucleophilic substitution in which an atom or Order of Reactivity: 9
10 Reaction Mechanism: 10
11 A) Nucleophilic Acyl Substitution Reactions of Acid Chlorides: Synthesis of acid chlorides: Reactions: 11
12 Mechanism: B) Nucleophilic Acyl Substitution Reactions of Acid Anhydrides: Synthesis: Reactions: 12
13 Mechanism: C) Nucleophilic Acyl Substitution Reactions of Carboxylic Acids: Reactions: Mechanism: 13
14 D) Nucleophilic Acyl Substitution Reactions of Esters: Hydrolysis:Cleavage of a bond by water Transesterfication: Conversion of one ester into another by replacing the OR group Reactions of esters: Mechanism: 14
15 Synthesis of Esters by Nucleophilic Acyl Substitution: E) Nucleophilic Acyl Substitution Reactions of Amides: Where are these reactions used? Polyamide: Polymer in which the structural repeating units are connected by amide linkages Polyester: Polymer in which the structural repeating units are connected by ester linkages 15
16 8.2.3 Addition Reactions Reductions with LiAlH 4 : Reactions with Grignard Reagents 16
17 Mechanism: Reactions Involving Carbanions A) Malonic Ester Synthesis Malonic Ester Synthesis: A method of preparing disubstituted acetic acids Mechanism: 17
18 B) Claisen Condensation: Claisen Condensation: A method for making β keto esters from esters with α hydrogens Mechanism: 18
19 Examples from Biology: 19
20 8.3 Amines Amine: Derivative of ammonia in which one or more hydrogens are replaced by organic groups Structure: Ammonia Primary Amine Secondary Amine Tertiary Amine Arylamine: Derivative of ammonia in which one or more hydrogens are replaced by aromatic rings Example: 20
21 8.3.1 Nomenclature General: alkyl-amine If you have a ring as substituent: If you have an unsaturated amine: 21
22 Can undergo hydrogen bonding Physical Properties > Decrease in hydrogen bonding Basicity of amines Amines are LEWIS BASES, they have a lone pair The lone pair can be shared to form salts: Amines are weak bases if dissolved in water you get an equilibrium: with an equilibrium constant pk b : The negative logarithm of the basicity constant > Weak base Increasing basicity Strong base 22
23 Relationship of structure and basicity in amines: - electron-releasing (donating) groups increase basicity - electron-withdrawing groups decrease basicity - aromatic amines are less basic than alkyl amines (resonance) - electron-donating groups on aromatic rings increase basicity Synthesis of Amines A) Reduction: Reduction: Introduction of hydrogen into a molecule, often resulting in the loss of oxygen or conversion of double bonds to single bonds 23
24 Reduction of aromatic nitro compounds Reduction of nitriles Reduction of amides 24
25 8.3.4 Amines as Nucleophiles Amines are effective nucleophiles than can react with alkylhalides The salt formed is called Quaternary Ammonium Salt Consecutive alkylation: Aromatic Diazonium Salts Diazonium salt: aromatic ring Preparation: Compound in which a molecule of nitrogen is bonded to an 25
26 Resonance form: Replacement reactions (Sandmeyer Reaction) 26
27 Coupling reactions: Diazonium salts can couple to HIGHLY activated aromatic rings General Reaction: Heterocyclic Amines Heterocycle: Cyclic compound where at least one ring atom is NOT carbon Piperidine Pyridine Pyrrolidine Pyrrole Alkaloids: humans Plant-produced nitrogenous bases that have physiological effects on 27
28 28
29 Summary of Chapter 6: Carboxylic Acids Nomenclature Physical Properties Acidity Preparation Derivatives of Carboxylic Acids Esters Amides Anhydrides Acid Chlorides Nomenclature Nucleophilic Acyl Substitution Preparation of Derivatives Reactivity of Derivatives Addition Reactions Reactions Containing Carbanion Amines Nomenclature Physical Properties Preparation Reactivity Sandmeyer Reaction Heterocycles Alkaloids 29
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