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Chapter 22: Problem 48

Structural and optical isomers can be drawn having the formula $\mathrm{C}_{5} \mathrm{H}_{11} \mathrm{F}$ . Give examples to illustrate these types of isomerism for \(\mathrm{C}_{5} \mathrm{H}_{11} \mathrm{F}\) . Why can't \(\mathrm{C}_{5} \mathrm{H}_{11} \mathrm{F}\) exhibit geometrical isomerism?

Short Answer

Expert verified
Structural isomers for C₅H₁₁F have different connectivities, such as CH₂F-CH₂-CH₂-CH₂-CH₃ and CH₃-CHF-CH₂-CH₂-CH₃. Optical isomers, like enantiomers, have the same structural formula but different spatial arrangements; for example, CH₃-CHF-CH₂-CH₂-CH₃ and its non-superimposable mirror image CH₃-CHF*-CH₂-CH₂-CH₃. Geometrical isomerism is not possible for C₅H₁₁F since it does not have any double bonds or ring structures.

Step by step solution

01

Define structural and optical isomers

Structural isomers (also called constitutional isomers) are molecules with the same molecular formula, but different bonding arrangements or connectivity between atoms. Optical isomers are molecules that are non-superimposable mirror images of each other (enantiomers), which means they have the same structural formula but differ in the arrangement of atoms in space.
02

Identify structural isomers for C₅H₁₁F

For C₅H₁₁F, we can have different structures with different connectivities. For example, we can have a molecule where the fluorine atom is attached to the first carbon atom and the other carbon atoms are attached linearly, like this: CH₂F-CH₂-CH₂-CH₂-CH₃ Alternatively, we can have a structure with the fluorine atom attached to the second carbon atom: CH₃-CHF-CH₂-CH₂-CH₃ These two structures are examples of structural isomers for C₅H₁₁F, as their atom connectivity differs.
03

Identify optical isomers for C₅H₁₁F

To identify optical isomers, we should look for chiral centers in the molecules (carbon atoms with four different substituents). For example, in the second structural isomer given above, the carbon atom with the fluorine atom attached (CHF) is a chiral center: CH₃-CHF-CH₂-CH₂-CH₃ The enantiomer of this molecule (its non-superimposable mirror image) would have the same connectivity, but a different spatial arrangement of the substituents: CH₃-CHF*-CH₂-CH₂-CH₃ (* denotes the chiral center) These two molecules are examples of optical isomers (enantiomers) for C₅H₁₁F.
04

Explain why C₅H₁₁F cannot exhibit geometrical isomerism

Geometrical isomers (also called cis-trans or E/Z isomers) differ from each other in the spatial arrangement of substituents around a double bond or in a cyclic structure. The formula C₅H₁₁F does not have any double bonds or ring structures, which means the molecules cannot have different geometrical arrangements of substituents around a double bond or within a cyclic structure. Therefore, geometrical isomerism is not possible for C₅H₁₁F.

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Most popular questions from this chapter

Three different organic compounds have the formula $\mathrm{C}_{3} \mathrm{H}_{8} \mathrm{O}$ . Only two of these isomers react with \(\mathrm{KMn} \mathrm{O}_{4}\) (a strong oxidizing agent). What are the names of the products when these isomers react with excess \(\mathrm{KMnO}_{4} ?\)

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