Chapter THREE Review Summary (Organic Chemistry 1, Chem0310 by Xinyu Liu)

(A) Key points for the exam

A1) Radical (Definition) / Carbon Radical Stability / Hyperconjugation

How is a radical generated? What is the relative trend of carbon radical (tertiary/secondary/primary/methyl)
stability? Can you use hyperconjugation to rationalize this trend?
(ref Questions 3-15, 3-16)

A2) Halogenation of Alkanes (Reaction Mechanism)

Given an alkane halogenation reaction (both starting materials and products provided), can you properly use
structures and organic arrows to illustrate the reaction mechanism? For a radical reaction, that consists of
three distinctive steps: initiation, propagation and termination steps.
(ref Question 3-13, 3-22, 3-35)

A3) Selectivity in the Halogenation of Alkanes

Given an alkane halogenation reaction (both starting materials and products provided), can you use the
Hammond postulate and the relative trend of carbon radical stability to rationalize why a certain halogenated
alkane is the preferred product in the given reaction? Can you also predict the outcome of a given alkane
halogenation reaction (only starting materials provided), i.e. what are the possible product(s) and which one
is the most favored product?
(ref. Questions 3-27, 29, 38, also read unit 3-8 (this unit is self-explanatory and it helps you appreciate the
importance of selectivity in a given organic reaction )

A4) Combustion of Alkanes

Heat of combustion of isomeric compounds is an indicator of their relative stabilities.
(ref Questions 3-33, 3-34)