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Chapter 8: Problem 15

There are three constitutional isomers with the molecular formula \(\mathrm{C}_{5} \mathrm{H}_{12}\). When treated with chlorine at \(300^{\circ} \mathrm{C}\), isomer A gives a mixture of four monochlorination products. Under the same conditions, isomer B gives a mixture of three monochlorination products, and isomer \(\mathrm{C}\) gives only one monochlorination product. From this information, assign structural formulas to isomers \(A, B\), and \(C\).

Short Answer

Expert verified
Question: Identify the structural formulas for isomers A, B, and C based on the given information about the number of monochlorination products each isomer yields. Answer: Isomer A is 2-Methylbutane, Isomer B is Pentane, and Isomer C is 2,2-Dimethylpropane.

Step by step solution

01

Find the constitutional isomers of C5H12

Draw the isomers of C5 on paper or use a molecular modeling kit. There are three constitutional isomers with the molecular formula C5H12: a) Pentane (n-pentane) b) 2-Methylbutane (isopentane) c) 2,2-Dimethylpropane (neopentane) Now let's analyze each isomer's monochlorination products.
02

Determine the number of possible monochlorination products for each isomer

Replace a hydrogen atom (H) with a chlorine atom (Cl) in each possible location on each isomer. a) Pentane: There are 3 unique sites for the H to be replaced by Cl, so it can form three monochlorination products. b) 2-Methylbutane: There are 4 unique sites for the H to be replaced by Cl, so it can form four monochlorination products. c) 2,2-Dimethylpropane: There are only 1 unique site for the H to be replaced by Cl, so it can form only one monochlorination product.
03

Assign structural formulas to isomers A, B, and C

Based on the monochlorination product information, we can assign each isomer to the corresponding structural formulas. Isomer A: Produces 4 monochlorination products, so it corresponds to 2-Methylbutane. Isomer B: Produces 3 monochlorination products, so it corresponds to Pentane. Isomer C: Produces 1 monochlorination product, so it corresponds to 2,2-Dimethylpropane.

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Most popular questions from this chapter

Water and dichloromethane are insoluble in each other. When each is added to a test tube, two layers form. Which layer is water and which is dichloromethane?

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