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Chapter 11: Problem 21

How many different isomers can be derived from ethylene if two hydrogen atoms are replaced by a fluorine atom and a chlorine atom? Draw their structures and name them. Indicate which are structural isomers and which are geometric isomers.

Short Answer

Expert verified
There are two different isomers that can be derived from ethylene by replacing two hydrogen atoms by a fluorine atom and a chlorine atom. These are 1-chloro-1-fluoroethene and 2-chloro-1-fluoroethene. Both are structural isomers of each other, and no geometric isomers are present.

Step by step solution

01

Understand the Structure of Ethylene

Ethylene, or ethene, has the molecular formula \(C_2H_4\). It consists of two carbon atoms double bonded to each other, with each carbon atom also attached to two hydrogen atoms. It's a planar molecule with a trigonal planar geometry around each carbon atom.
02

Generate Isomers from Ethylene by Replacing Hydrogen Atoms

When replacing two hydrogen atoms in ethylene by a fluorine atom and a chlorine atom, two different isomers can be generated: \n1. Both atoms on the same carbon atom, \n2. The atoms on different carbon atoms. \nThese are considered structural isomers as they have the same molecular formula, but differ in the connectivity of their atoms.
03

Draw Structures and Name Isomers

1. Structural Isomer 1 has the structure \(H_2C=CF(Cl)\), and can be named as 1-chloro-1-fluoroethene. \n2. Structural Isomer 2 has the structure \(HC=CH(Cl)F\), and is named as 2-chloro-1-fluoroethene. There are no geometric isomers present in this case.

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Most popular questions from this chapter

The structural isomers of pentane, \(\mathrm{C}_{5} \mathrm{H}_{12}\), have quite different boiling points (see Example 11.1 ). Explain the observed variation in boiling point, in terms of structure.

The combustion of \(20.63 \mathrm{mg}\) of compound \(\mathrm{Y}\), which contains only \(\mathrm{C}, \mathrm{H},\) and \(\mathrm{O}\), with excess oxygen gave \(57.94 \mathrm{mg}\) of \(\mathrm{CO}_{2}\) and \(11.85 \mathrm{mg}\) of \(\mathrm{H}_{2} \mathrm{O}\). (a) Calculate how many milligrams of \(\mathrm{C}, \mathrm{H},\) and \(\mathrm{O}\) were present in the original sample of \(Y\). (b) Derive the empirical formula of Y. (c) Suggest a plausible structure for \(\mathrm{Y}\) if the empirical formula is the same as the molecular formula.

When a mixture of methane and bromine vapor is exposed to light, this reaction occurs slowly: $$\mathrm{CH}_{4}(g)+\mathrm{Br}_{2}(g) \longrightarrow \mathrm{CH}_{3} \mathrm{Br}(g)+\mathrm{HBr}(g)$$Suggest a mechanism for this reaction.

Generally aldehydes are more susceptible to oxidation in air than are ketones. Use acetaldehyde and acetone as examples and show why ketones such as acetone are more stable than aldehydes in this respect.

Draw Newman projections of four different conformations of butane. Rank them in stability.
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