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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

Fats and oils are names for the same class of compounds, called triglycerides, which contain three ester groups in which \(\mathrm{R}, \mathrm{R}^{\prime},\) and \(\mathrm{R}^{\prime \prime}\) represent long hydrocarbon chains. (a) Suggest a reaction that leads to the formation of a triglyceride molecule, starting with glycerol and carboxylic acids (see p. 398 for structure of glycerol). (b) In the old days, soaps were made by hydrolyzing animal fat with lye (a sodium hydroxide solution). Write an equation for this reaction. (c) The difference between fats and oils is that at room temperature, the former are solid and the latter are liquids. Fats are usually produced by animals, whereas oils are commonly found in plants. The melting points of these substances are determined by the number of \(\mathrm{C}=\mathrm{C}\) bonds (or the extent of unsaturation) present- -the larger the number of \(\mathrm{C}=\mathrm{C}\) bonds, the lower the melting point and the more likely the substance is a liquid. Explain. (d) One way to convert liquid oil to solid fat is to hydrogenate the oil, a process by which some or all of the \(\mathrm{C}=\mathrm{C}\) bonds are converted to \(\mathrm{C}-\mathrm{C}\) bonds. This procedure prolongs shelf life of the oil by removing the more reactive \(\mathrm{C}=\mathrm{C}\) group and facilitates packaging. How would you carry out such a process (that is, what reagents and catalyst would you employ)? (e) The degree of unsaturation of oil can be determined by reacting the oil with iodine, which reacts with the \(\mathrm{C}=\mathrm{C}\) as follows: The procedure is to add a known amount of iodine to the oil and allow the reaction to go to completion. The amount of excess (unreacted) iodine is determined by titrating the remaining iodine with a standard sodium thiosulfate \(\left(\mathrm{Na}_{2} \mathrm{~S}_{2} \mathrm{O}_{3}\right)\) solution: $$\mathrm{I}_{2}+2 \mathrm{Na}_{2} \mathrm{~S}_{2} \mathrm{O}_{3} \longrightarrow \mathrm{Na}_{2} \mathrm{~S}_{4} \mathrm{O}_{6}+2 \mathrm{NaI}$$ The number of grams of iodine that reacts with \(100 \mathrm{~g}\) of oil is called the iodine number. In one case, \(43.8 \mathrm{~g}\) of \(\mathrm{I}_{2}\) were treated with \(35.3 \mathrm{~g}\) of corn oil. The excess iodine required \(20.6 \mathrm{~mL}\) of \(0.142 \mathrm{M} \mathrm{Na}_{2} \mathrm{~S}_{2} \mathrm{O}_{3}\) for neutralization. Calculate the iodine number of the corn oil.

The combustion of \(3.795 \mathrm{mg}\) of liquid \(\mathrm{B}\), which contains only \(\mathrm{C}, \mathrm{H},\) and \(\mathrm{O},\) with excess oxygen gave 9.708 \(\mathrm{mg}\) of \(\mathrm{CO}_{2}\) and \(3.969 \mathrm{mg}\) of \(\mathrm{H}_{2} \mathrm{O}\). In a molar mass determination, \(0.205 \mathrm{~g}\) of \(\mathrm{B}\) vaporized at \(1.00 \mathrm{~atm}\) and \(200.0^{\circ} \mathrm{C}\) and occupied a volume of \(89.8 \mathrm{~mL}\). Derive the empirical formula, molar mass, and molecular formula of \(\mathrm{B}\) and draw three plausible structures.

Draw all the structural isomers of compounds with the formula \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{Cl}_{2}\). Indicate which isomers are chiral and give them systematic names.

Complete this equation and identify the products: $$\mathrm{HCOOH}+\mathrm{CH}_{3} \mathrm{OH} \longrightarrow$$

What are functional groups? Why is it logical and useful to classify organic compounds according to their functional groups?
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