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Ch.23 - Organic and Biological Chemistry
All textbooksMcMurry 8th EditionCh.23 - Organic and Biological ChemistryProblem 84
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Chapter 23, Problem 84

Which of the following compounds are capable of cis–trans isomerism? (a) 1-Hexene (b) 2-Hexene (c) 3-Hexene

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1
Identify the structural requirement for cis-trans isomerism: a compound must have a double bond with each carbon of the double bond attached to two different groups.
Examine 1-Hexene: The double bond is between the first and second carbon atoms. Since the first carbon is attached to two hydrogen atoms, it cannot have cis-trans isomers.
Examine 2-Hexene: The double bond is between the second and third carbon atoms. Each of these carbons is attached to different groups, allowing for cis-trans isomerism.
Examine 3-Hexene: The double bond is between the third and fourth carbon atoms. Each of these carbons is attached to different groups, allowing for cis-trans isomerism.
Conclude which compounds can exhibit cis-trans isomerism based on the analysis of their structures.
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Related Practice
Open Question
(a) Draw an orbital overlap picture of ethane (CH3CH3), assuming both carbon atoms are sp3 hybridized. What are the C–H bond angles in this drawing? (b) Draw an orbital overlap picture of ethane, assuming both carbon atoms are sp2 hybridized. What are the C–H bond angles in this drawing? (c) The real structure of ethane is like the picture you drew in part (a). Use VSEPR theory to explain why your picture from part (a) makes a more stable molecule than your picture in part (b).
Open Question
Draw an orbital overlap picture of methane (CH₄) with the carbon in sp3 hybridization and an orbital overlap picture of a molecule with carbon in sp2 hybridization. Explain why the carbon atom in methane is more stable in sp3 hybridization than in sp2 hybridization.
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Unlike palmerolide A (Problem 23.80), which has a large ring, a cyclic molecule with only six atoms can only have a cis double bond, but not a trans double bond. Give a line drawing of a cyclic molecule with six carbon atoms and a cis double bond. Explain why it cannot have a trans double bond.
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What does it mean to say that fats and oils are triacylglycerols?
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Draw the structure of glycerol myristate, a fat made from glycerol and three myristic acid molecules (see Table 23.3).