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Chapter 11: Problem 57

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.

Short Answer

Expert verified
The structural isomers of C4H8Cl2 are 1,1-dichlorobutane, 1,2-dichlorobutane, 1,3-dichlorobutane, 2,2-dichlorobutane, 1,2-dichloro-2-methylpropane, and 1,1-dichloro-2-methylpropane, among which only 1,2-dichloro-2-methylpropane is chiral.

Step by step solution

01

Draw all possible isomers of C4H8Cl2

Begin by drawing diagrams for every possible structural isomer of the molecular formula. Four molecules of carbon (C) can form a straight chain or a branched chain. Two chlorine atoms (Cl) can be placed in different positions on these chains, leading to different structural isomers. The possibilities are 1,1-dichlorobutane, 1,2-dichlorobutane, 1,3-dichlorobutane, 2,2-dichlorobutane, 1,2-dichloro-2-methylpropane, and 1,1-dichloro-2-methylpropane.
02

Identify chiral isomers

Look for chiral centers (carbon atoms bonded to four different groups) in the isomers. In this case, only 1,2-dichloro-2-methylpropane has a chiral center. So, it is the only chiral isomer.
03

Assign systematic names to the isomers

The systematic names of the isomers are assigned following IUPAC nomenclature. They are: \[1,1\text{-}dichlorobutane for the first isomer, 1,2\text{-}dichlorobutane for the second isomer, 1,3\text{-}dichlorobutane for the third isomer, 2,2\text{-}dichlorobutane for the fourth isomer, 1,2\text{-}dichloro\text{-}2\text{-}methylpropane for the fifth isomer, and 1,1\text{-}dichloro\text{-}2\text{-}methylpropane for the last isomer.\] Correspondingly, these names describe the structure, positions of functional groups, and the branched chain in the molecule.

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Most popular questions from this chapter

A compound having the molecular formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\) does not react with sodium metal. In the presence of light, the compound reacts with \(\mathrm{Cl}_{2}\) to form three compounds having the formula \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{OCl}\). Draw a structure for the original compound that is consistent with this information.

Amines are Bronsted bases. The unpleasant smell of fish is due to the presence of certain amines. Explain why cooks often add lemon juice to suppress the odor of fish (in addition to enhancing the flavor).

Given these data $$\begin{array}{c}\mathrm{C}_{2} \mathrm{H}_{4}(g)+3 \mathrm{O}_{2}(g) \longrightarrow 2 \mathrm{CO}_{2}(g)+2 \mathrm{H}_{2} \mathrm{O}(l) \\\\\Delta H^{\circ}=-1411 \mathrm{~kJ} / \mathrm{mol} \\\2 \mathrm{C}_{2} \mathrm{H}_{2}(g)+5 \mathrm{O}_{2}(g) \longrightarrow 4 \mathrm{CO}_{2}(g)+2 \mathrm{H}_{2} \mathrm{O}(l) \\\\\Delta H^{\circ}=-2599 \mathrm{~kJ} / \mathrm{mol} \\\\\mathrm{H}_{2}(g)+\frac{1}{2} \mathrm{O}_{2}(g) \longrightarrow \mathrm{H}_{2} \mathrm{O}(l) \\\\\Delta H^{\circ}=-285.8 \mathrm{~kJ} / \mathrm{mol}\end{array}$$ calculate the heat of hydrogenation for acetylene: $$\mathrm{C}_{2} \mathrm{H}_{2}(g)+\mathrm{H}_{2}(g) \longrightarrow \mathrm{C}_{2} \mathrm{H}_{4}(g)$$

Draw all possible isomers for the molecule \(\mathrm{C}_{4} \mathrm{H}_{8}\).

The compound \(\mathrm{CH}_{3}-\mathrm{C} \equiv \mathrm{C}-\mathrm{CH}_{3}\) is hydrogenated to an alkene using platinum as the catalyst. If the product is the pure cis isomer, what can you deduce about the mechanism?
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