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Ch 5 Alkyl Halides; Substitution and Elimination reactions Title: Mar 28 10:49 AM (1 of 36)

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Page 1: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Ch 5 Alkyl Halides;

Substitution and Elimination reactions

Title: Mar 28 ­ 10:49 AM (1 of 36)

Page 2: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Is Organic Chemistry onlybased upon Memorization?

Title: Mar 28 ­ 10:49 AM (2 of 36)

Page 3: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

No, Organic Chemistryis based upon Understanding!

Title: Mar 28 ­ 10:49 AM (3 of 36)

Page 4: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

The Relationship between STRUCTURE and REACTIVITY

Title: Mar 28 ­ 10:49 AM (4 of 36)

Page 5: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

The Relationship between STRUCTURE and REACTIVITY

Title: Mar 28 ­ 10:49 AM (5 of 36)

Page 6: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

ALKYL HALIDES

SUBSTITUTION ELIMINATION

Title: Mar 28 ­ 10:49 AM (6 of 36)

Page 7: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Leaving group

Title: Mar 28 ­ 10:49 AM (7 of 36)

Page 8: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (8 of 36)

Page 9: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (9 of 36)

Page 10: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

General Case

Title: Mar 28 ­ 10:49 AM (10 of 36)

Page 11: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

reaction of a nucleophile and an alkyl halide

Title: Mar 28 ­ 10:49 AM (11 of 36)

Page 12: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

reaction of a nucleophile and an alkyl halide

Title: Mar 28 ­ 10:49 AM (12 of 36)

Page 13: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (13 of 36)

Page 14: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions

Title: Mar 28 ­ 10:49 AM (14 of 36)

Page 15: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (15 of 36)

Page 16: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (16 of 36)

Page 17: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

What is(are) the major product(s) of the following reaction?

(A) (B)

(A) & (B)

Title: Mar 28 ­ 10:49 AM (17 of 36)

Page 18: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

INVERSIONof stereochemistry

Stereochemistry of the reaction

Title: Mar 28 ­ 10:49 AM (18 of 36)

Page 19: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (19 of 36)

Page 20: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (20 of 36)

Page 21: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Rate of Reaction =

reactions have 2nd order Kinetics

Title: Mar 28 ­ 10:49 AM (21 of 36)

Page 22: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (22 of 36)

Page 23: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (23 of 36)

Page 24: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (24 of 36)

Page 25: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (25 of 36)

Page 26: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (26 of 36)

Page 27: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Tertiary alkyl halides DO NOT undergo reactions

Title: Mar 28 ­ 10:49 AM (27 of 36)

Page 28: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (28 of 36)

Page 29: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (29 of 36)

Page 30: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (30 of 36)

Page 31: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Rate of Reaction =

reactions have 1st order Kinetics

Title: Mar 28 ­ 10:49 AM (31 of 36)

Page 32: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

What is(are) the major product(s) of the following reaction?

(A) & (B)

(A) (B)

ol ol

Title: Mar 28 ­ 10:49 AM (32 of 36)

Page 33: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (33 of 36)

Page 34: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (34 of 36)

Page 35: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (35 of 36)

Page 36: Alkyl Halides - faculty.kfupm.edu.sa · Only alkyl halides with sp3 hybridized head carbons undergo nucleophilic subsitiution reactions Title: Mar 28  10:49 AM (14 of 36)

Title: Mar 28 ­ 10:49 AM (36 of 36)