Nil

1. p. 566
O
C
H
H
Formaldehyde
O
C
CH3
H
Acetaldehyde
C
H
O
Benzaldehyde
Common Names of Simple Aldehydes and Ketones

2. p. 566
Common Names of Carbonyl substituents

3. p. 567
Preparation of Aldehydes and Ketones : Review
1. Oxidation of 1 alcohols to aldehydes:
a. PCC
b. Dess-Martin Periodinane

4. p. 567
Preparation of Aldehydes and Ketones : Review
1. Oxidation of 1 alcohols to aldehydes:
a. PCC
b. Dess-Martin Periodinane

5. p. 567
Preparation of Aldehydes and Ketones : Review
2. Oxidation of 2 alcohols to ketones:
a. CrO3 , H2SO4
b. K2Cr2O7, H2SO4
c. PCC
d. Dess - Martin

6. p. 567
Preparation of Aldehydes and Ketones : Review
2. Oxidation of 2 alcohols to ketones:
a. CrO3 , H2SO4
b. K2Cr2O7, H2SO4
c. PCC
d. Dess - Martin

7. p. 568
Preparation of Aldehydes and Ketones : Review
3. Aryl aldehydes and ketones:
Friedel – Crafts Acylation

8. p. 568
Preparation of Aldehydes and Ketones : Review
3. Aryl aldehydes and ketones:
Friedel – Crafts Acylation

9. p. 568
Preparation of Aldehydes and Ketones: New
1. From Acid Chlorides via Acyl Transfer
Using R2CuLi (Section 16.4)

10. p. 568
Preparation of Aldehydes and Ketones: New
1. From Acid Chlorides via Acyl Transfer
Using R2CuLi (Section 16.4)
2. From Esters
Reduction with DIBAH (Section 16.6)

11. p. 568
Oxidation of Aldehydes : Review
a. CrO3, H2SO4
b. K2Cr2O7, H2SO4

12. p. 568
Oxidation of Aldehydes : Review
a. CrO3, H2SO4
b. K2Cr2O7, H2SO4

13. Fig. 14-3, p. 571
Nucleophilic Additions to Aldehydes and Ketones
I. Reactivity
1. Aldehydes vs. ketones
2. Aromatic vs. aliphatic

14. p. 571

15. Fig. 14-3, p. 571
Nucleophilic Additions to Aldehydes and Ketones
I. Reactivity
1. Aldehydes vs. ketones
2. Aromatic vs. aliphatic
3. The Burgi – Dunitz angle

16. Fig. 14-3, p. 571
Nucleophilic Additions to Aldehydes and Ketones

17. The Burgi-Dunitz(-Lehn-Wipff) Angle:
Molecular orbital representaiton
Tetrahedron 1974 30 (12): 1563–1572.

18. Fig. 14-3, p. 571
Nucleophilic Additions to Aldehydes and Ketones
II. Types of Nucleophiles
1. Anionic
2. Neutral

19. Fig. 14-3, p. 571
Nucleophilic Additions to Aldehydes and Ketones
II. Types of Nucleophiles
1. Anionic
2. Neutral
i. Water
ii. Alcohols
iii. 1 amines
iv. 2 amines

20. Professor Gilbert Stork
Stork was born in Brussels, Belgium, and received his secondary
education in France. The B.S. (1942) and Ph.D. (1945) were obtained at
the Universities of Florida and Wisconsin respectively. He was on the
Harvard faculty (1946-53), then joined the Columbia faculty where he was
instrumental in building its strong organic group and is currently Eugene
Higgins Professor Emeritus. Stork's many awards include the ACS
Award in Pure Chemistry (1957), the ACS Award for Creative Work in
Synthetic Organic Chemistry (1967), the Arthur C. Cope Award (1980), the
Willard Gibbs Medal (1982), the National Medal of Science (1982), the
Tetrahedron Prize (1985), the Roger Adams Award (1991) and the Wolf
Prize (1996). In 2001 he published the first completely stereoselective
total synthesis of quinine.
http://chem.tufts.edu/AMichael-Bio.html

21. Fig. 14-3, p. 571
Reactions of Ylides with Aldehydes
I. The Wittig Reaction
1. Generation and nature of ylides
2. The Metathesis reaction
a. Stereochemistry

22. The Truth about the Wittig reaction
J. Am. Chem. Soc. 1973, 95, 5778.

23. Fig. 14-3, p. 571
Reactivity of a,b-unsaturated carbonly compounds
1. Electrophilic sites
2. Hard-soft acid-base theory
3. Examples

24. p. 589

25. Professor Author Michael
Born in Buffalo NY in 1855, he studied chemistry at Heidelberg under Robert
Bunsen (1811-1899) and at Berlin under August Wilhelm Hofmann (1818-1892).
He then studied under Adolphe Wurtz (1817-1884) in Paris and Dimitri Ivanoviè
Mendeleev (1834-1907) in St Petersburg, but never bothered to take a degree.
He was made Professor of Chemistry at Tufts College near Boston. In 1889, he
married one of his most brilliant students, (1857-1904), one of the few women
organic chemists Helen Cecilia DeSilver Abbott in this period. After a failed
attempt to run the chemistry department at Clark University in Worcester,
Massachusetts, in 1891, he spent three years working with his wife in his
private laboratory on the Isle of Wight before returning to Tufts. After he retired
from Tufts in 1907, Michael set up another private laboratory at Newton Center
near Boston. In 1912 he was appointed a Professor of Chemistry, without
lecturing duties, at Harvard University. Arthur Michael died in 1942.
http://chem.tufts.edu/AMichael-Bio.html

26. Professor Henry Gilman
(May 9, 1893 – Nov 7, 1986). Born in Boston, Massachusetts, he received his B.
S. (1915), an M. S. (1916), and a Ph.D. (1918) in Chemistry from Harvard
University. For his pre-doctoral work he studied in Europe at Zurich
Polytechnikum, the Sorbonne in Paris, and at Oxford in London. Dr. Gilman
began his career at the University of Illinois as an Instructor of Chemistry in 1919.
Later that year, he accepted the position of Assistant Professor (1919 - 1920) at
Iowa State College (University). By 1923 Dr. Gilman had been promoted to full
Professor teaching all the Organic Chemistry courses at Iowa State College.
His main area of research was in the Organometallic Chemistry area of Grignard
reagents where he developed numerous Organometallic reagents, including the
dialkyllithium reagent which bears his name.
http://www.lib.iastate.edu/spcl/exhibits/150/template/gilman.html

27. End