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Chapter 8: Q39E (page 220)

Use your general knowledge of alkene chemistry to suggest a mechanism for the following reaction.

Short Answer

Expert verified

Mechanism of the reaction is:

Fig

]No reactions included

Step by step solution

01

Alkenes

It is an unsaturated hydrocarbon compound. Alkenes are having double bonds between carbon atoms and the hybridization of carbon atoms having double bond is . Alkenes are also known as olefins. In an aliphatic chain the alkenes are defined as symmetrical alkenes and asymmetrical alkenes.

02

Example

Symmetrical alkenes are those alkenes which are having same number of carbon atoms on both the sides of double bond and asymmetrical alkenes are those which are having unequal number of carbon atoms on both the sides of double bond.

03

Step by Step Mechanism of the reaction

Step 1: Most substituted double bond will attack on mercury(II) acetate, cyclic mercurinium ion will form and OAC will release.

Step 2: In this step double bond will attack on the carbocation and another cyclic ring will form.

Step 3: OAC that was released in first step will now abstract the proton and the final product will form.

fig

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Most popular questions from this chapter

Simmons鈥揝mith reaction of cyclohexene with diiodomethane gives asingle cyclopropane product, but the analogous reaction of cyclohexene with 1,1-diiodoethane gives (in low yield) a mixture of two isomeric methylcyclopropane products. What are the two products, and how do they differ?

How would you distinguish between the following pairs of compounds using simple chemical tests? Tell what you would do and what you would see.

(b) 2-Hexene and benzene

Compound A has the formula C8H8. It reacts rapidly with KMnO4to giveCO2 and a carboxylic acid, B (C7H6O2), but reacts with only 1 molar equivalent of H2on catalytic hydrogenation over a palladium catalyst. On hydrogenation under conditions that reduce aromatic rings, 4 equivalents ofH2 are taken up and hydrocarbon C (C8H16)is produced. What are the structures of A, B, and C? Write the reactions.

Dichlorocarbene can be generated by heating sodium trichloroacetate.

Propose a mechanism for the reaction, and use curved arrows to indicate

the movement of electrons in each step. What relationship does

your mechanism bear to the base-induced elimination of HCl from

chloroform?

The reaction of cyclohexene with mercury(II) acetate in CH3OH rather than

H2O, followed by treatment with NaBH4, yields cyclohexyl methyl ether rather than cyclohexanol. Suggest a mechanism.
See all solutions

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