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Chapter 10: Q.25. (page 410)

Question: Draw the products of each reaction and indicate their stereochemistry.

Short Answer

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Answer

Step by step solution

01

Step 1:Reaction of an alkene with a dihalide

The treatment of an alkene with dihalide in the presence of water gives enantiomers.

02

Formation of products for a and b

a. The reaction of cyclopentene with NBS in the presence of DMSO and water is shown below:

Product formation in a

b. The reaction of 1-methylcyclohex-1-enewith dichloride in the presence of water is shown below:

Product formation in b

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Most popular questions from this chapter

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-.

Question: Give the structure corresponding to each name.

a. (E)-4-ethylhept-3-ene

b. 3,3-dimethylcyclopentene

c. 4-vinylcyclopentene

d. (Z)-3-isopropylhept-2-ene

e. cis-3,4-dimethylcyclopentene

f. 1-isopropyl-4-propylcyclohexene

g. 3,4-dimethylcyclohex-2-enol

h. 3,5-diethylhex-5-en-3-ol

Question: Explain why A is a stable compound but B is not.

Question: Like other electrophiles, carbocations add to alkenes to form new carbocations, which can then undergo substitution or elimination reactions depending on the reaction conditions. With this in mind, consider the following reactions of nerol, a natural product isolated from lemon grass and other plant sources. Treatment of nerol with TsOH forms α-terpineol as the major product, whereas treatment of nerol with chlorosulfonic acid, HSO3Cl , forms a constitutional isomer, α-cyclogeraniol. Write stepwise mechanisms for both processes. Each mechanism involves the addition of an electrophile—a carbocation— to a double bond.

Question: Draw a stepwise mechanism for the following reaction. Draw the transition state for each step.
See all solutions

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