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Chapter 22: Problem 115

The two isomers having the formula \(\mathrm{C}_{2} \mathrm{H}_{6} \mathrm{O}\) boil at \(-23^{\circ} \mathrm{C}\) and \(78.5^{\circ} \mathrm{C}\). Draw the structure of the isomer that boils at \(-23^{\circ} \mathrm{C}\) and of the isomer that boils at \(78.5^{\circ} \mathrm{C}\).

Short Answer

Expert verified
The structure of the isomer that boils at -23°C is dimethyl ether (\(\ce{CH3-O-CH3}\)), and the structure of the isomer that boils at 78.5°C is ethanol (\(\ce{CH3-CH2-OH}\)).

Step by step solution

01

Determine possible isomers

First, we need to determine all possible isomers with the molecular formula \(\mathrm{C}_{2} \mathrm{H}_{6} \mathrm{O}\). In this case, there are two possible structures: ethanol and dimethyl ether.
02

Analyze the isomers' boiling points

Next, we need to analyze which isomer would correspond to which boiling point. Boiling points are affected by factors such as molecular weight and the strength of intermolecular forces. - Ethanol: (\(\mathrm{CH}_{3}\mathrm{CH}_{2}\mathrm{OH}\)) has a hydroxyl (-OH) group, which forms strong hydrogen bonds with other ethanol molecules, leading to a higher boiling point. - Dimethyl ether: (\(\mathrm{CH}_{3}\mathrm{OCH}_{3}\)) has an oxygen atom bonded to two methyl groups and does not form hydrogen bonds as effectively as ethanol, leading to a lower boiling point.
03

Match the isomers with the boiling points

Based on our analysis in Step 2, we can conclude that: - The isomer that boils at -23°C is dimethyl ether because it has weaker intermolecular forces (less hydrogen bonding) than ethanol. - The isomer that boils at 78.5°C is ethanol because it has stronger intermolecular forces (more hydrogen bonding) than dimethyl ether.
04

Draw the structures

Lastly, we will draw the structures of the isomers: - The structure of dimethyl ether (boiling at -23°C): \(\ce{CH3-O-CH3}\) - The structure of ethanol (boiling at 78.5°C): \(\ce{CH3-CH2-OH}\)

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Most popular questions from this chapter

Which of the following polymers would be stronger or more rigid? Explain your choices. a. The copolymer of ethylene glycol and terephthalic acid or the copolymer of 1,2 -diaminoethane and terephthalic acid \((1,2-\) diaminoethane \(=\mathrm{NH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\) ) b. The polymer of \(\mathrm{HO}-\left(\mathrm{CH}_{2}\right)_{6}-\mathrm{CO}_{2} \mathrm{H}\) or that of O=C(O)c1ccc(O)cc1 c. Polyacetylene or polyethylene (The monomer in polyacetylene is ethyne.)

For each of the following, fill in the blank with the correct response(s). All of the following pertain to nucleic acids. a. The substance in the nucleus of the cell that stores and transmits genetic information is DNA, which stands for b. The basic repeating monomer units of DNA and RNA are called c. The pentose deoxyribose is found in DNA, whereas is found in RNA. d. The basic linkage in DNA or RNA between the sugar molecule and phosphoric acid is a phosphate e. The bases on opposite strands of DNA are said to be to each other, which means the bases fit together specifically by hydrogen bonding to one another. f. In a strand of normal DNA, the base found paired with the base adenine, whereas is always found paired with cytosine. g. A given segment of the DNA molecule, which contains the molecular coding for a specific protein to be synthesized, is referred to as a- h. During protein synthesis, RNA molecules attach to and transport specific amino acids to the appropriate position on the pattern provided by RNA molecules. i. The codes specified by are responsible for assembling the correct primary structure of proteins.

Name all the aldehydes and ketones that have the formula \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O} .\)

Consider the following reactions. For parts \(\mathrm{b}-\mathrm{d}\), see Exercise \(62 .\) a. When \(\mathrm{C}_{5} \mathrm{H}_{12}\) is reacted with \(\mathrm{Cl}_{2}(g)\) in the presence of ultraviolet light, four different monochlorination products form. What is the structure of \(\mathrm{C}_{5} \mathrm{H}_{12}\) in this reaction? b. When \(\mathrm{C}_{4} \mathrm{H}_{8}\) is reacted with \(\mathrm{H}_{2} \mathrm{O}\), a tertiary alcohol is produced as the major product. What is the structure of \(\mathrm{C}_{4} \mathrm{H}_{8}\) in this reaction? c. When \(\mathrm{C}_{7} \mathrm{H}_{12}\) is reacted with \(\mathrm{HCl}\), 1 -chloro-1-methylcyclohexane is produced as the major product. What are the two possible structures for \(\mathrm{C}_{7} \mathrm{H}_{12}\) in this reaction? d. When a hydrocarbon is reacted with \(\mathrm{H}_{2} \mathrm{O}\) and the major product of this reaction is then oxidized, acetone (2-propanone) is produced. What is the structure of the hydrocarbon in this reaction? e. When \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\) is oxidized, a carboxylic acid is produced. What are the possible structures for \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\) in this reaction?

Ethylene oxide, is an important industrial chemical. Although most ethers are unreactive, ethylene oxide is quite reactive. It resembles \(\mathrm{C}_{2} \mathrm{H}_{4}\) in its reactions in that addition reactions occur across the \(\mathrm{C}-\mathrm{O}\) bond in ethylene oxide. a. Why is ethylene oxide so reactive? (Hint: Consider the bond angles in ethylene oxide as compared with those predicted by the VSEPR model.) b. Ethylene oxide undergoes addition polymerization, forming a polymer used in many applications requiring a nonionic surfactant. Draw the structure of this polymer.
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