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Chapter 10: Q.20. (page 404)

Question: Draw all stereoisomers formed when 1,2-dimethylcyclohexene is treated with HCl. Label pairs of enantiomers.

Short Answer

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Answer

All the stereoisomers are shown hereunder.

Step by step solution

01

Electrophilic addition of H+

The pi-electron density attacks the acidic hydrogen from the HX molecule, leading to the cleavage of pi-bond and the formation of a carbocation.

02

Enantiomers and diastereomers

Enantiomers are mirror images of a compound that are not superimposable on each other.

Diastereomers are not mirror images of any compound.

03

Products of the given reactions

The reactions of all the stereoisomers of 1,2-dimethylcyclohexene with HCl are shown hereunder.

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Most popular questions from this chapter

Question: Draw all stereoisomers formed in each reaction.

a.

b.

c.

Question: (a) Label the carbon–carbon double bond in A as E or Z. (b) Draw the products (including stereoisomers) formed when A is treated with H2O in the presence of H2SO4.

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: How many rings and π bonds does a compound with molecular formula C10H14 possess? List all possibilities.

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.
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