Figure 3-9 compares the reactions of CI with the primary and secondary hydrogens of propane. (a) Draw
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(a) Draw a similar diagram comparing the reactions of Br∙ with the primary and secondary hydrogens of propane.
(b) Which among the transition states of these reactions would you call '"early," and which "late"?
(c) Judging from the locations of the transition states of these reactions along the reaction coordinate, should they show greater or lesser radical character than do the corresponding transition states for chlorination (Figure 3-9)?
(d) Is your answer to (c) consistent with the selectivity differences between Cl∙ reacting with propane and Br∙ reacting with propane? Explain.
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Organic Chemistry structure and function
ISBN: 978-1429204941
6th edition
Authors: K. Peter C. Vollhardt, Neil E. Schore
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