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Chapter 10: Q.29. (page 415)

Question: Draw the constitutional isomer formed when the following alkenes are treated with each set of reagents: [1] H2O,H2SO4; or [2] BH3followed by H2O2,HO-.

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01

Step 1:Addition reaction of an alkene

Hydroboration-oxidation reaction involves the formation of a primary alcohol, whereas acid-catalyzed hydration reaction involves the formation of a secondary alcohol.

02

Formation of products for a, b and c

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Most popular questions from this chapter

Question: Bromoetherification, the addition of the elements of Br and OR to a double bond, is a common method for constructing rings containing oxygen atoms. This reaction has been used in the synthesis of the polyether antibiotic monensin (Problem 21.37). Draw a stepwise mechanism for the following intramolecular bromoetherification reaction.

Question: Less stable alkenes can be isomerized to more stable alkenes by treatment with strong acid. For example, 2,3-dimethylbut-1-ene is converted to 2,3-dimethylbut-2-ene when treated with . Draw a stepwise mechanism for this isomerization process.

Question: What alkene can be used to prepare each alkyl halide or dihalide as the exclusive or major product of an addition reaction?

a.

b.

c.

d.

Question: Draw all stereoisomers formed in each reaction.

a.

b.

c.

Question: Use the Hammond postulate to explain why (CH3)2C=CH2reacts faster than CH3CH=CH2 in electrophilic addition of HX.
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