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Chapter 11: Problem 77

Write the structural formulas of the alcohols with the formula \(\mathrm{C}_{6} \mathrm{H}_{13} \mathrm{O}\) and indicate those that are chiral. Show only the \(\mathrm{C}\) atoms and the \(-\mathrm{OH}\) groups.

Short Answer

Expert verified
Considering the given alcohol formula \(C_6H_{13}O\), there are four isomers of this alcohol. However, only the isomers with the OH group attached to the second, third or fourth carbons in the chain are chiral, because they have a carbons attached to four different groups.

Step by step solution

01

Construct the Structure

Based on the formula \(C_6H_{13}O\), construct a structure which has six carbon atoms as a chain and a hydroxy or \(-OH\) group attached to one of those carbon atoms. Now connect the remaining hydrogen atoms, such that each carbon atom forms four bonds in total (including the bond with the hydroxy group).
02

Generate Isomers

There may be more than one way to arrange the hydrogen atoms around the carbon atoms while maintaining balance. Each different arrangement of atoms represents a different alcohol, these are known as isomers. Explore all the possible isomers by changing the position of the hydroxy group in the carbon chain. Remember that the first and last carbon in the chain can't have the hydroxy group because they don't create a chirality center.
03

Identify Chiral Alcohols

A molecule is chiral if it cannot be superimposed on its mirror image. In terms of carbon atoms, a carbon atom in the molecule is a chiral center if it is bonded to four different groups. Identify the stereocenters (carbon atoms attached to four different groups) in the generated isomers. Molecules having one or more stereocenter(s) are chiral.

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Most popular questions from this chapter

Give examples of a chiral substituted alkane and an achiral substituted alkane.

Isopropyl alcohol is prepared by reacting propene \(\left(\mathrm{CH}_{3} \mathrm{CHCH}_{2}\right)\) with sulfuric acid, followed by treatment with water. (a) Show the sequence of steps leading to the product. What is the role of sulfuric acid? (b) Draw the structure of an alcohol that is an isomer of isopropyl alcohol. (c) Is isopropyl alcohol a chiral molecule? (d) What property of isopropyl alcohol makes it useful as a rubbing alcohol?

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: $$\mathrm{C}_{2} \mathrm{H}_{2}(g)+\mathrm{H}_{2}(g) \longrightarrow \mathrm{C}_{2} \mathrm{H}_{4}(g)$$

Alkenes exhibit geometric isomerism because rotation about the \(\mathrm{C}=\mathrm{C}\) bond is restricted. Explain.

Write structural formulas for these compounds: (a) trans-2-pentene, (b) 2-ethyl-1-butene, (c) 4 -ethyltrans-2-heptene, (d) 3 -phenyl- 1 -butyne.
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