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 1o, 2o, and 3o 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? (donít 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.







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



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