ORGANIC - BROWN 8E CH CARBOXYLIC ACIDS.

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1 RGANIC - BRWN 8E CH CARBXYLIC ACIDS!!

2 RGANIC - BRWN 8E CH CARBXYLIC ACIDS CNCEPT: CARBXYLIC ACID NMENCLATURE IUPAC: Replace alkane -e with Substituents are located using Common: Memorize the first 5 common names Substituents are located using Negative anions (deprotonated) are named using the suffix EXAMPLE: Give both the correct IUPAC and common name for the following molecule. ( ) Formic Acid ( ) Acetic Acid ( ) Propionic Acid ( ) Butyric Acid ( ) Valeric Acid Page 2

3 RGANIC - BRWN 8E CH CARBXYLIC ACIDS PRACTICE: Provide the IUPAC name for the following compound. PRACTICE: Provide the IUPAC name for the following compound. Br H H Page 3

4 RGANIC - BRWN 8E CH CARBXYLIC ACIDS CNCEPT: CARBXYLIC ACID NMENCLATURE Diacids: Memorize the first 3 common names Page 4

5 RGANIC - BRWN 8E CH CARBXYLIC ACIDS PRACTICE: Provide the common name for the following compound. H H PRACTICE: Provide the IUPAC name for the following compound. H H Page 5

6 RGANIC - BRWN 8E CH CARBXYLIC ACIDS CNCEPT: REDUCTIN Reducing agents are used to reduce molecules These reagents add hydrogens across π-bonds. Unsaturated hydrocarbons and carbonyls can be reduced. General Mechanism: Nucleophilic addition of hydrogen Reducing agents add to ALL π-bonds present. Multiple equivalents of hydrogen will react if possible. LiAlH4 is a strong reducing agent. It is able to reduce ANY carbonyl compound into alcohol EXAMPLE: Draw the products of the following molecules reacted with LiAlH4 NaBH4 is a weak reducing agent. It can only add equivalent of oxygen and can only reduce CH and ketones EXAMPLE: Draw the products of the following molecules reacted with NaBH4 Page 6

7 RGANIC - BRWN 8E CH CARBXYLIC ACIDS CNCEPT: FISCHER ESTERIFICATIN MECHANISM Also known as acid-catalyzed esterification, this is one of the more important mechanisms in this course. General Reaction: Mechanism: Page 7

8 RGANIC - BRWN 8E CH CARBXYLIC ACIDS CNCEPT: CH DERIVATIVES AND NUCLEPHILIC ACYL SUBSTITUTIN Carboxylic acid derivatives are defined as any carbonyl with a single electronegative group (-Z) in the α-position. These follow unique nucleophilic mechanism due to the presence of a leaving group, called NAS. By definition, they can ALL be hydrolyzed to a carboxylic acid using water with acid or base. Nitriles also fall into this category due to their ability to be hydrolyzed = -Cl, -CR -R, -H, - NH3 General Carbonyl Mechanisms: Page 8

9 RGANIC - BRWN 8E CH CARBXYLIC ACIDS CNCEPT: NUCLEPHILIC ACYL SUBSTITUTIN THE THREE RULES Most of the formulas governing the conversion of carboxylic acid derivatives can be simplified into the following 3 Rules: RULE #1 The general reactions for these conversions are as follows: RULE #2 More reactive acyl compounds can be easily into less reactive ones. The reactivity of carbonyls toward NAS depends upon the strength of the RULE #3 The Carboxylic Acid Conversions Page 9

10 RGANIC - BRWN 8E CH CARBXYLIC ACIDS PRACTICE: Determine the major product for the following reaction. PRACTICE: Determine the major product for the following reaction. PRACTICE: Determine the major product for the following reaction. PRACTICE: Determine the major product for the following reaction. Page 10

11 RGANIC - BRWN 8E CH CARBXYLIC ACIDS CNCEPT: SPECIFIC CARBXYLIC ACID CNVERSINS Synthesis of Acid Chloride: Synthesis of Amides: Dehydration of Amides: Hydrolysis of Nitriles: Page 11

12 RGANIC - BRWN 8E CH CARBXYLIC ACIDS CNCEPT: DECARBXYLATIN β-carbonyl carboxylic acids easily decarboxylate when heated, producing C2 gas. Mechanism: EXAMPLE: Predict the correct structure for the final product. Page 12

13 RGANIC - BRWN 8E CH CARBXYLIC ACIDS PRACTICE: Provide the mechanism for the following reaction. H Page 13

14 RGANIC - BRWN 8E CH CARBXYLIC ACIDS PRACTICE: Which carbonyl group will undergo decarboxylation most readily? C H HC C H H C Page 14