Compounds A through H are isomeric bromoalkanes with the molecular formula C5H11br. With your team, draw all eight constitutional isomers. Indicate any stereo-center) (s), but do not label it (them) as R or S until you have completed your analysis. Using the data below, assign structures to A through H. Divide the problem into equal parts to share the effort of finding a solution. Reconvene and discuss your analysis. At this point, you should indicate the stereochemistry with wedged and hashed lines as appropriate.
• 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.