310_11 - Organic Lecture Series CH 310 N LECTURE 11...

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Organic Lecture Series 1 CH 310 N LECTURE 11 Textbook Assignment: Chapter 17 Carboxylic Acids Homework (for credit): Problem Set 3-Posted Today’s Topics: Nucleophilic Acyl Substitution Rxns Notice & Announcements: EXAM 1: Pick up papers in the Hall-after class Organic Lecture Series 2 Functional Functional Derivatives of Derivatives of Carboxylic Acids Carboxylic Acids
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Organic Lecture Series 3 Nucleophilic Nucleophilic acyl acyl substitution: substitution: an addition-elimination sequence resulting in substitution of one nucleophile for another Tetrahedral carbonyl addition intermediate - + + C Nu R C Y R C R O Y O O :Nu - :Y - Substitution product : Characteristic Reactions Characteristic Reactions Organic Lecture Series 4 + (cat) Fischer Fischer Esterifications Esterifications
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Organic Lecture Series 5 in the general reaction, the leaving group, as an anion, illustrates an important point: the weaker the base, the better the leaving group R 2 N - RO - O RCO - X - Increasing basicity Increasing leaving ability Characteristic Reactions Characteristic Reactions Organic Lecture Series 6 – halide ion is the weakest base and the best leaving group; acid halides are the most reactive toward nucleophilic acyl substitution – amide ion is the strongest base and the poorest leaving group; amides are the least reactive toward nucleophilic acyl substitution Characteristic Reactions Characteristic Reactions
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Organic Lecture Series 7 Reaction with H Reaction with H 2 O O - Acid Chlorides Acid Chlorides – low-molecular-weight acid chlorides react rapidly with water – higher molecular-weight acid chlorides are less soluble in water and react less readily These are hydrolysis reactions- “breaking of bonds with water” CH 3 CCl O H 2 OC H 3 COH O HCl + + Acetyl chloride Organic Lecture Series 8 Reaction with H Reaction with H 2 O O - Anhydrides Anhydrides – low-molecular-weight acid anhydrides react readily with water to give two molecules of carboxylic acid
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310_11 - Organic Lecture Series CH 310 N LECTURE 11...

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