Draw the products of the two step reaction sequence shown below. Ignore inorganic byproducts. HO PBr3 Select to Draw thiol DMF cyclohexane NaH
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The attack of PBr3 on alcohol follows SN2 reaction.
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- The Favorskii reaction involves treatment of an -bromo ketone with base to yield a ring-contracted product. For example, reaction of 2-bromocyclohexanone with aqueous NaOH yields cyclopentanecarboxylic acid. Propose a mechanism.The following molecule was formed by a Robinson annulation reaction. What reactants were used?When a 2, 6-disubstituted allyl phenyl ether is heated in an attempted Claisen rearrangement, migration occurs to give the p-allyl product as the result of two sequential pericyclic reactions. Explain.
- Draw the major organic product(s) of the following reaction. If no reaction is expected, write "N.R." Clearly show stereochemistry if appropriate.(a) What happens when CH3—O—CH<sub3 is heated with HI?(b) Explain mechanism for hydration of acid catalyzed ethene :CH2 = CH2 + HzO CH3—CH,—OHDraw the major organic product(s) of the following reactions. If no reaction is expected, write "N.R." Clearly show stereochemistry if appropriate.
- When a cyclic ketone reacts with diazomethane, the next larger cyclic ketone is formed. This is called a ring-expansion reaction. Draw a mechanism forthe following ring-expansion reaction.When 2-bromo-3-phenylbutane is treated with sodium methoxide, two alkenes result (by E2 elimination). The Zaitsevproduct predominates.(a) Draw the reaction, showing the major and minor productsThe reaction of 2-ethyl-1-pentene with Br2, with H2 + Pd/C, or with R2BH/THF followed by aqueous HO- + H2O2 leads to a racemic mixture. Explain why a racemic mixture is obtained in each case.