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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

Draw all the possible structural isomers for the molecule having the formula \(\mathrm{C}_{7} \mathrm{H}_{7} \mathrm{Cl}\). The molecule contains one benzene ring.

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.

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.

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

You are given two bottles, each containing a colorless liquid. You are told that one liquid is cyclohexane and the other is benzene. Suggest one chemical test that would enable you to distinguish between these two liquids.
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