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Chapter 10: PROBLEM 10.55 (page 422)

Question: Using cis- and trans-hex-3-ene, demonstrate that the addition of HCl is not a stereospecific reaction. Draw the structure of the stereoisomers formed from each alkene.

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01

Stereospecific reaction  

A stereospecific reaction gives either R or S isomer in a greater yield. The racemic mixture does not contain a stereospecific product as it has R and S isomers in equal amounts.

02

Addition of HCl to an alkene

The alkene forms an intermediate when it reacts with HCl. It is due to the protonation of the double bond. Protonation gives a positive charge on the carbon present on the other side of the double bond.

This positive charge is highly stable, and therefore, chloride ion attacks it.

03

Explanation

Cis and trans-hex-3-ene react with HCl to give the same racemic mixture. Therefore, the products are not stereospecific.

Reaction of cis-hex-3-ene and trans-hex-3-ene with HCl

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Most popular questions from this chapter

Question: Lactones, cyclic esters such as compound A, are prepared by halolactonization, an addition reaction to an alkene. For example, iodolactonization of B forms lactone C, a key intermediate in the synthesis of prostaglandin (Section 4.15). Draw a stepwise mechanism for this addition reaction.

Question: Although naturally occurring unsaturated fatty acids generally have the Z configuration, elaidic acid, a C18 fatty acid having an E double bond, is present in processed foods such as margarine and cooking oils. Predict how the melting point of elaidic acid compares with the melting points of stearic and oleic acids (Table 10.2).

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 伪-terpineol as the major product, whereas treatment of nerol with chlorosulfonic acid, HSO3Cl , forms a constitutional isomer, 伪-cyclogeraniol. Write stepwise mechanisms for both processes. Each mechanism involves the addition of an electrophile鈥攁 carbocation鈥� to a double bond.

Question: Alkene A can be isomerized to isocomene, a natural product isolated from goldenrod, by treatment with TsOH. Draw a stepwise mechanism for this conversion. (Hint: Look for a carbocation rearrangement.)

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