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Chapter 26: Problem 53

Draw the \(E\) and \(Z\) isomers of (a) 2 -chloro-2-butene; (b) 3 -methyl- 2 -pentene.

Short Answer

Expert verified
In the E isomers, the higher priority groups are on opposite sides of the double bond, while in the Z isomers, they are on the same side. This priority is determined by comparing the atomic numbers of the directly connected atoms.

Step by step solution

01

Analyze the molecular structure

Before drawing isomers, it's necessary to understand the molecular structure of the organic compounds. For 2-chloro-2-butene, there are four carbons in the skeleton with a double bond between the second and third carbon and a chlorine substituent on the second carbon. For 3-methyl-2-pentene, there are five carbons in the skeleton with a double bond between the second and third carbon and a methyl substituent on the third carbon.
02

Draw the E isomer

To draw the E isomer, identify the atoms directly connected to the carbons with the double bond. Compare their atomic numbers; the group with the atom of higher atomic number gets priority. Arrange the molecule so that the higher priority groups are on opposite sides of the double bond. For 2-chloro-2-butene, chlorine (atomic number 17) will be on one side, and the methyl group (a combination of carbons and hydrogens; carbon has atomic number 6) on the opposite side. For 3-methyl-2-pentene, the ethyl group (another combination of carbons and hydrogens) has higher priority than the methyl group, so they should be on opposite sides of the double bond.
03

Draw the Z isomer

For the Z isomer, the higher priority groups will be on the same side of the double bond. For the given compounds, place the higher priority groups (chlorine for 2-chloro-2-butene and the ethyl group for 3-methyl-2-pentene) on the same side of the double bond.

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Most popular questions from this chapter

Write structural formulas corresponding to these condensed formulas. (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHBrCHBrCH}_{3}\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CCH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (c) \(\left(\mathrm{C}_{2} \mathrm{H}_{5}\right)_{2} \mathrm{CHCH}=\mathrm{CHCH}_{2} \mathrm{CH}_{3}\).

Supply a name or structural formula for each of the following. (a) phenylacetylene (b) \(m\) -dichlorobenzene

Indicate why each of these names is incorrect, and give a correct name. (a) 3 -pentene; (b) pentadiene; (c) 1-propanone; (d) bromopropane; (e) 2,6 -dichlorobenzene; (f) 2 -methyl- 3 -pentyne

Alkenes (olefins) and cyclic alkanes (alicyclics) each have the generic formula \(\mathrm{C}_{n} \mathrm{H}_{2 n}\). In what important ways do these types of compounds differ structurally?

A compound with the same hydrogen-to-carbon ratio as cyclobutane is (a) \(\mathrm{C}_{4} \mathrm{H}_{10} ;\) (b) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{C}=\mathrm{CCH}_{3} ;\) (d) \(\mathrm{C}_{6} \mathrm{H}_{6}\).
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