CHAPTER SIX

Alkenes: Structure and Reactivity

Learning Objectives: Calculate degrees of unsaturation from molecular formula. Identify and name cis/trans and E/Z isomers of alkenes. Become proficient in use of Cahn-Ingold-Prelog rules for E/Z specification. Know how to rank similar alkene structures in terms of relative energies. Be able to discuss reaction mechanisms for alkene reactions including use of curvey arrow representations, structures of transition states and intermediates, carbocation rearrangements, and energy diagrams. Write carbocation structures and rank carbocations in terms of relative energy. Understand importance of Hammond postulate.

Calculate the degree of unsaturation (Section 6.2)

6.1 - 6.3, 6.18 - 6.21

Nomenclature and isomers (Section 6.3)

6.4 - 6.6, 6.22 - 6.24, 6.26, 6.27, 6.29, 6.30

Draw cis-trans isomers of alkenes (Section 6.5)

6.7, 6.8

Cahn-Ingold-Prelog rules and E,Z nomenclature (Section 6.6)

6.9 - 6.11, 6.25, 6.38 - 6.41

Stability of alkenes (Section 6.7)

6.12, 6.32 - 6.35

Mechanisms and prediction of products from reactions (Section 6.8 - 6.12)

6.13 - 6.15, 6.17, 6.36, 6.37, 6.43, 6.44

Transition states and Hammond Postulate (Section 6.11)

6.16, 6.46, 6.47