Carboxylic Acids (Part 2): Synthesis of Esters

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1 J. G. Rudick CHE 322: rganic Chemistry A Spring 2017 Lecture 22 (3/20/17) Carboxylic Acids (Part 2): Synthesis of Esters Chapter 20 in Loudon, M.; Parise, J. rganic Chemistry, 6th Ed. W. H. Freeman: New York, NY, 2016 Prof. Jon Rudick ffice Hours: CHEM 775 Mondays 1:30 2:30p Tuesdays 1:30 2:30p Thursdays 2:30p 3:30p 1

2 Esterification: synthesis of an ester from an alcohol and a carboxylic acid RH + H R + H 2 Synthesis of a Fragrant Ester (CHE 327, Experiment 7) H + H CH 3 H 2 S 4 CH 3 + H 2 butanol ethanoic acid (acetic acid) butyl ethanoate (butyl acetate) dor description of butyl ethanoate (butyl acetate) from Bananas image from: https://www.theartofdoingstuff.com/wp-content/uploads/2013/03/banana.jpg 2

3 J. G. Rudick Clicker Question Spring 2017 Pre-lecture 21 Quiz Question Choose the structure that matches the expected product of this reaction. H + H H 2 S 4? H H A B C D 3

4 Esterification: synthesis of an ester from an alcohol and a carboxylic acid RH + H R + H 2 Synthesis of a Fragrant Ester (CHE 327, Experiment 7) H + H H 2 S H 2 2-methylpropanol propanoic acid 2-methylpropyl propanoate dor description of 2-methylpropyl propanoate (isobutyl propionate) from Bananas image from: https://www.theartofdoingstuff.com/wp-content/uploads/2013/03/banana.jpg Bubble gum image from: 4

5 J. G. Rudick Clicker Question Spring 2017 Choose the alcohol and carboxylic acid required for this reaction.? H 2 S 4 + H 2 A H + H C H + H B H + H D H + H 5

6 Esterification: synthesis of an ester from an alcohol and a carboxylic acid RH + H R + H 2 Synthesis of a Fragrant Ester (CHE 327, Experiment 7) butanol H + H propanoic acid H 2 S 4 dor description of butyl propanoate (butyl propionate) from Bananas image from: https://www.theartofdoingstuff.com/wp-content/uploads/2013/03/banana.jpg Cherries image from: 6 butyl propanoate + H 2

7 J. G. Rudick Clicker Question Spring 2017 (Pre-lecture Quiz Question) Choose the name that matches the alcohol required for this reaction.? H 2 S 4 A. 1-Methyl butanol B. 2-Methyl butanol C. 3-Methyl butanol D. 2-Methyl pentanol E. 3-Methyl pentanol 7 + H 2

8 Esterification: synthesis of an ester from an alcohol and a carboxylic acid RH + H R + H 2 Synthesis of a Fragrant Ester (CHE 327, Experiment 7) H 2 S 4 H H methylbutanol ethanoic acid (acetic acid) 3-methylbutyl ethanoate + H 2 dor description of 3-methylbutyl ethanoate (isoamyl acetate) from Bananas image from: https://www.theartofdoingstuff.com/wp-content/uploads/2013/03/banana.jpg 8

9 J. G. Rudick Clicker Question Spring 2017 Which scheme best illustrates the first step in the mechanism of acid-catalyzed esterification? A H H + H 2 B H H + H H C H H+ H 2 D H + H H 9

10 Acid-catalyzed Esterification (Fisher Esterification) Mechanism H H + H H H H H H 10

11 Acid-catalyzed Esterification (Fisher Esterification) Mechanism H H + H H RH H H H R H 2 + H R H H R H H R + H + H tetrahedral intermediate H R R H + + R 11

12 Acid-catalyzed Esterification (Fisher Esterification) Br H H 2 S 4 + CH 3 H Br 88% yield CH 3 J. Am. Chem. Soc. 2005, 127,

13 Acid-catalyzed Esterification (Fisher Esterification) H C 6 H 4 Br H + H H C 6 H 4 Br CH 3 H H H CH 3 H C 6 H 4 Br H 2 + H CH 3 C 6 H 4 Br H H CH 3 H C 6 H 4 Br H CH 3 + H + H C 6 H 4 Br tetrahedral intermediate H CH 3 C 6 H 4 Br H + + H 3 C C 6 H 4 Br 13

14 J. G. Rudick Clicker Question Spring 2017 n a series of nucleophiles in which the nucleophilic atoms are from the same period [row] of the periodic table, there is a rough correlation of nucleophilicity with [pka of the conjugate acid]. Loudon, M.; Parise, J. rganic Chemistry, 6th Ed. W. H. Freeman: New York, NY, 2016; p 398 Choose the sequence that correctly ranks the nucleophilicity of these anions from highest to lowest. decr. nucleophilicity (decr. pka of conjugate acid) Ac A. F > Ac > Ph > Me B. Ph > Me > F > Ac C. Ac > Ph > Me > F D. Me > Ph > Ac > F E. F > Me > Ph > Ac 14

15 n a series of nucleophiles in which the nucleophilic atoms are from the same period [row] of the periodic table, there is a rough correlation of nucleophilicity with [pka of the conjugate acid]. Nucleophile N C Me Ph N3 Ac F log k (SN2) * pka of the conjugate acid Decreasing Nucleophilicity * log k (SN2) is an index for nucleophilicity Loudon, M.; Parise, J. rganic Chemistry, 6th Ed. W. H. Freeman: New York, NY, 2016; pp

16 Esterification by Alkylation of the Carboxylate Anion usually involves alkyl halides that are very reactive in SN2 reactions (a.k.a., Hunsdiecker reaction) R X + H base polar aprotic solvent Examples of alkyl halides that are very reactive in SN2 reactions R H 3 C Br Br Cl (SN1) 16

17 Esterification by Alkylation of the Carboxylate Anion usually involves an SN2 reaction mechanism (a.k.a., Hunsdiecker reaction) H + B + B H + R X SN2 Transition State R X δ- δ- H H R + X Alkyl halides that form very stable carbocations (e.g., triphenylmethyl) involve an SN1 mechanism 17

18 Esterification by Alkylation of the Carboxylate Anion usually involves alkyl halides that are very reactive in SN2 reactions (a.k.a., Hunsdiecker reaction) R X + H base polar aprotic solvent Using carboxylate salts can avoid the need for a base R R X + M + M + = Na +, K +, Cs + polar aprotic solvent R 18

19 J. G. Rudick Clicker Question Spring 2017 Which alkyl halide will react most easily (i.e.,fastest) to give you an ester? H +? K 2 C 3 R Br Cl Br A B C D 19

20 Esterification by Alkylation of the Carboxylate Anion usually involves alkyl halides that are very reactive in SN2 reactions (a.k.a., Hunsdiecker reaction) H K 2 C 3 + CH 3 CH 3 88% yield J. rg. Chem. 2003, 68, H + Br K 2 C 3 81% yield J. rg. Chem. 2013, 78,

21 Lactones are the products when hydroxy acids undergo intramolecular acid-catalyzed esterification H H H + + H 2 K eq = 145 lactone (cyclic ester) H H H + + H 2 K eq = 445 lactone (cyclic ester) For any other ring size, the equillibrium is unfavorable (i.e., Keq < 1). Loudon, M.; Parise, J. rganic Chemistry, 6th Ed. W. H. Freeman: New York, NY, 2016; p

22 J. G. Rudick Clicker Question Spring 2017 Br n Na n + NaBr Which lactone forms fastest? A (n = 1) B (n = 2) C (n = 3) D (n = 4) E (n = 5) 22

23 Five membered Rings form Fastest! Dependence of the rate of lactone formation on ring size is representative of many ring-closing reactions Br n Na n + NaBr relative rate ring size 5-membered (n = 3) >> ~ >>> 6-membered (n = 4) 4-membered (n = 2) Larger rings (i.e., 7-membered or more) close slower than 3-membered rings 23 3-membered (n = 1) J. Am. Chem. Soc. 1973, 95,

24 odolactonization Chem. Soc. Rev. 1979, 8, H NaHC 3 (aq) H B + + B H 24

25 J. G. Rudick Clicker Question Spring 2017 Pre-lecture Quiz Question Choose the structure that matches the expected major product of the reaction. C 2 H 2 NaHC 3? A B C D E 25

26 odolactonization 2 C 2 H NaHC 3 backside attack H X H not backside attack 26

27 J. G. Rudick Lecture 22 Ended Here Spring 2017 Clicker Question Answers 4. C. 6. D. 8. C. 10. B. 15. D. 20. C. 23. C. 25. B. 27

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