CHM 2211C Sample Name: __ _______________________

Chapter 10 Part E: Chapter 10 Exercises: 20 points

(your instructor will tell you which problems to do, or do the ones circled on your paper)

#4 Mechanisms

Question #1 Nomenclature/Isomers of Alkyl Halides

Problems: 10.1, 10.2, 10.3, 10.17, 10.18, 10.19

10.3 Draw and name all monochloro products you would expect from the radical chlorination of 2-methylpentane.

Which, if any are chiral?

Question #2 Alkyl Halide Application & Theory Questions plus questions on qualitative alkyl halides (who do it?):

Problems: 10.4, 10.5, 10.6, 10.9. 10.10, 10.20,

10.4 Taking the relative reactivities of 1^o, 2^o, and 3^o hydrogen atoms into account, what products would you expect to obtain from monochlorination of 2-methylbutane?

What would be the approximate percentage of each product be? (don’t forget to take into account the number of each hydrogen type.)

Question #3 R-1/R-2 Reactions of Alkyl Halides:

Problems: 10.7, 10.8, 10.21, 10.32

10.7 What products would you expect of the following alkanes with NBS? If more than one product is formed, show structures of all.

(a)

(b)

Question #4 Mechanisms, Synthesis,& Challenging Questions

Problems: Work either 10.30 or 10.40

10.30: Draw the resonance structure for the benzyl radical, C₆H₅CH₂·

Or

10.40: Phenols, compounds that have an –OH group bonded to a benzene, are relatively acidic because their anions are stabilized by resonance. Draw resonance structures for the phenoxide ion.