Compounds A through H are isomeric bromoalkanes with the molecular formula C5H11br. With your team, draw all
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• Treatment of compounds A through G with NaCN in DMF followed second-order kinetics and showed the following relative rates:
A ≅ B > > D ≅ E > F > > G
• Compound H does not undergo the SN2 reaction under the preceding conditions.
• Compounds C, D, and F were found to be optically active, each having S absolute configuration at the stereo-center. Substitution reactions of D and F with NaCN in DMF proceeded with inversion of configuration, while treatment of C in the same way proceeded with retention of configuration.
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Related Book For
Organic Chemistry structure and function
ISBN: 978-1429204941
6th edition
Authors: K. Peter C. Vollhardt, Neil E. Schore
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