Concept explainers
Interpretation:
Major product of the sequence of reactions shown is to be determined.
Concept introduction:
The OH group in an alcohol is a poor leaving group as the hydroxide ion is a strong base. For substitution reactions, therefore, it is necessary to convert it to a good leaving group. One way to do this is to sulfonate the alcohol using a reagent such as tosyl chloride. This results in the replacement of the hydrogen in the alcoholic OH by the tosyl group. The bulky tosylate is an excellent leaving group. Further, as the reaction does not occur at the carbon atom, the configuration at the carbon is preserved if it is an asymmetric carbon. The tosylate can then be treated with a bulky, non-nucleophilic base to induce an E2 elimination. E2 elimintation involves elimination of the leaving group and a proton anticoplanar to it. Only the E isomer of the corresponding
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Organic Chemistry: Principles and Mechanisms (Second Edition)
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- Predict the major products of each of the following reactions. Draw the complete detailed mechanism that leads to the formation of these products. Letters D and Earrow_forwardDraw the complete, detailed mechanism for the reaction shown here and draw the major organic product. NH3 C,H15N H2O, Aarrow_forwardDraw a mechanism to account for the formation of the NaOH product in the reaction shown here. Hint: Under these A conditions, deprotonation of a propargylic (C=C-CH) carbon is reversible.arrow_forward
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- Draw a detailed mechanism for the following reaction and include the major productarrow_forwardDraw the complete, detailed mechanism for the reaction shown here and, using the mechanism, predict the major product. TSOH is a strong acid. -NH2 НО ? TSOH, C6H6, Aarrow_forwardThe reaction shown here is a halosulfonation, which is a useful variation of the sulfonation reaction. Draw the complete mechanism for this reaction.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning