Advanced Organic Chemistry: Carbonyl Reactivity

In this installment of the Synthesis Workshop Advanced Organic Chemistry course, Patrick Deneny joins us to give an overview of carbonyl reactivity.

References (in order of appearance):
Fundamentals of Organic Chemistry, 7th ed., Brooks/Cole Cengage Learning, 2011.
Organic Chemistry, 2nd ed., Oxford University Press, 2012.
Chemistry of the carbonyl group: A step-by-step approach to understanding organic reaction mechanisms, Wiley, 2018
J. Am. Chem. Soc. 1964, 86, 1089
J. Russ. Phys. Chem. Soc. 1911, 43, 582; Lieb. Ann. Chem. 1912, 394, 86; J. Am. Chem. Soc.1964, 86, 2909;
Chem. Ber. 1913, 46, 1837; Org. React. 1975, 22, 401.
J. Chem. Soc. 1946, 39; Tetrahedron Lett. 1968, 9, 3363; Tetrahedron Lett. 1975, 16, 2647; Tetrahedron Lett. 1979, 20, 399; J. Org. Chem. 1983, 48, 4155; J. Am Chem. Soc. 1991, 113, 7277; Tetrahedron 1978, 34, 1651.
Tetrahedron, 1974, 30, 1563; Acc. Chem. Res. 1983, 16, 153; C. R. Acad. Sci. 1900, 130, 1322; Organometallics 2009, 28, 1598.
Tetrahedron Lett., 1968, 9, 2199; J. Am. Chem. Soc. 1973, 95, 6146; Tetrahedron Lett. 1976, 17, 155.
J. Am. Chem. Soc. 1952, 74, 5828; Chem. Rev., 1999, 99, 1191; Tetrahedron Lett. 1994, 35, 8537;
J. Am. Chem. Soc. 1983, 105, 4833; J. Am. Chem. Soc. 1968, 90, 4011; Tetrahedron Lett. 1984, 25, 729
Chemistry of the carbonyl group: A step-by-step approach to understanding organic reaction mechanisms, Wiley, 2018;
J. Am. Chem. Soc. 1964, 86, 2105; J. Am. Chem. Soc. 1981, 103, 5393.
J. Chem. Soc. 1936, 623; Tetrahedron 1976, 32, 2979.
; J. Org. Chem. 1963, 28, 3362; Tetrahedron 1976, 32, 2979; J. Am. Chem. Soc. 1961, 83, 13, 2965.
J. Am. Chem. Soc. 1981, 103, 2127; J. Am. Chem. Soc. 1982, 104, 1737; Tetrahedron, 2014, 70, 2207; RSC Adv. 2016, 6, 30498; Tetrahedron Lett. 1981, 22, 3815; Synthesis, 2008, 2008, 3707.
J. Am. Chem. Soc. 2011, 133, 11936; J. Am. Chem. Soc. 2013, 135, 16853.
Bull Chim. Soc. Fr. 1872, 436; J. Am. Chem. Soc. 1973, 95, 3310; J. Org. Chem. 2016, 81, 5631; Synthesis, 1991, 2, 795.
J. Am. Chem. Soc. 1957, 79, 1920; Tetrahedron Lett. 1975, 16, 1225; J. Am. Chem. Soc. 1979, 101, 6120; J. Org. Chem. 1980, 45, 1066; J. Am. Chem. Soc. 1989, 111, 3441.
J. Am. Chem. Soc. 1979, 101, 6120; J. Am. Chem. Soc. 1981, 103, 2127; J. Am. Chem. Soc. 1981, 103, 3099;
Angew. Chem. Int. Ed. 2014, 53, 2692; Chem. Commun. 2021, 57, 3171.
J. Am. Chem. Soc. 1954, 76, 2029; J. Am. Chem. Soc. 1963, 85, 207; J. Am. Chem. Soc. 1970, 92, 4261.
J. Am. Chem. Soc. 2000, 122, 2395; J. Am. Chem. Soc. 2001, 123, 12911; Chem. Rev. 2007, 107, 5471; Angew. Chem. Int. Ed. 2005, 44, 794; Angew. Chem. Int. Ed. 2005, 44, 4212; J. Am. Chem. Soc. 2005, 127, 18296; Synlett 2012, 23, 953.
Angew. Chem. Int. Ed. 1979, 18, 239.
Angew. Chem. Int. Ed. 1965, 4, 1007; J. Org. Chem. 1966, 31, 4097; J. Org. Chem. 1975, 40, 231; Synthesis, 1977, 1977, 357; Acc. Chem. Res. 2004, 37, 365.
Ann. Pharm. 1832, 3, 249; Ann. Pharm. 1839, 31, 329; J. Chem. Soc. 1903, 83, 995.
J. Pharm. Soc. Jpn. 1943, 63, 296; J. Am. Chem. Soc. 1958, 80, 3719; Chem. Lett. 2008, 37, 534; J. Org. Chem. 2009, 74, 23, 9214; Beilstein J. Org. Chem. 2016, 12, 444.

[lorenzmayer]

could not have wished for a better summary of one OC-semester, really great work 🙌

[thelocalsage]

this one is super good so far, really enjoying the review! carbonyl chemistry was a unit i struggled with in my advanced synthesis course but this makes it seem much simpler

[Felixkeeg]

This was a great overview! I'll be refering my students to this next semester

[twitterforandriod]

I don't even go to college anymore and I was a aeronautical program do I never got to do chemistry let along organic chemistry! Thank you for making these lovely videis