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Chapter 16: Problem 325

Give each of the following structures IUPAC names: (a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHOH}\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{CHOH}-\mathrm{CH}_{3}\) (c) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CHOH}-\mathrm{CH}_{3}\); (d) \(\mathrm{CH}_{3}-\mathrm{CH}_{2} \mathrm{COH}\left(\mathrm{CH}_{3}\right)_{2}\);

Short Answer

Expert verified
The IUPAC names for the given structures are: (a) 2,2-dimethylethanol (b) 2-methyl-2,3-dimethylpropanol (c) 3-butanol (d) 2-propanol-3,3-dimethyl

Step by step solution

01

Find the IUPAC Name for: \(\left(\mathrm{CH}_{3}\right)_{2}\mathrm{CHOH}\)

1. The parent chain contains two carbon atoms, so the base name is "ethane." 2. The presence of a hydroxyl group makes it an alcohol, changing the suffix "-ane" to "-anol." 3. Since there are only two carbons, the hydroxyl group must be in position 1. There are also two methyl groups attached to the second carbon atom. 4. Combine the elements of the name: 2,2-dimethylethanol.
02

Find the IUPAC Name for: \(\left(\mathrm{CH}_{3}\right)_{3}\mathrm{C}-\mathrm{CHOH}-\mathrm{CH}_{3}\)

1. The parent chain contains three carbon atoms, so the base name is "propane." 2. The presence of a hydroxyl group in the second carbon makes it an alcohol, changing the suffix "-ane" to "-anol." 3. Number the carbon atoms: The hydroxyl group is in position 2. There are also three methyl groups attached to the first carbon atom. 4. Combine the elements of the name: 2-methyl-2,3-dimethylpropanol.
03

Find the IUPAC Name for: \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CHOH}-\mathrm{CH}_{3}\)

1. The parent chain contains four carbon atoms, so the base name is "butane." 2. The presence of a hydroxyl group in the third carbon makes it an alcohol, changing the suffix "-ane" to "-anol." 3. Number the carbon atoms: The hydroxyl group is in position 3. 4. Combine the elements of the name: 3-butanol.
04

Find the IUPAC Name for: \(\mathrm{CH}_{3}-\mathrm{CH}_{2}\mathrm{COH}\left(\mathrm{CH}_{3}\right)_{2}\)

1. The parent chain contains three carbon atoms, so the base name is "propane." 2. The presence of a hydroxyl group on the second carbon makes it an alcohol, changing the suffix "-ane" to "-anol." 3. Number the carbons atoms: The hydroxyl group is in position 2. There are also two methyl groups attached to the third carbon atom. 4. Combine the elements of the name: 2-propanol-3,3-dimethyl.

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Most popular questions from this chapter

Explain how the following alcohols are named using the IUPAC system of nomenclature:

Indicate how you would synthesize each of the following substances from the given organic starting materials and other necessary organic or inorganic reagents. Specify reagents and conditions. (b) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{CH}_{2} \mathrm{Br}\) from \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHO}\) from \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{CH}_{3}\) (d) \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{CH}_{2} \mathrm{OCH}_{3}\) from ethylene

Would you expect optically active 1-deuterioethanol to react with HBr and yield 1-deuterioethy1 bromide with inversion of configuration, or with racemization? Explain.

A naive graduate student attempted the preparation of \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CDBrCH}_{3}\) from \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CDOHCH}_{3}\) by heating the deuterio-alcohol with \(\mathrm{HBr}\) and \(\mathrm{H}_{2} \mathrm{SO}_{4}\). He obtained a product having the correct boiling point, but a careful examination of the spectral properties by his research director showed that the product was a mixture of \(\mathrm{CH}_{3} \mathrm{CHDCHBrCH}_{3}\) and \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CDBrCH}_{3}\). What happened?

When allowed to react with aqueous HBr, 3 -buten \(-2-\circ 1\) \(\left(\mathrm{CH}_{3} \mathrm{CHOHCH}=\mathrm{CH}_{2}\right)\) yields not only 3 -bromo-1-butene \(\left(\mathrm{CH}_{3} \mathrm{CHBrCH}=\mathrm{CH}_{2}\right)\) but also 1 -bromo-2-butene \(\left(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{Br}\right)\) (a) How do you account for these results? (b) Predict the product of the reaction between \(\mathrm{HBr}\) and 2 -buten-1-o1 \(\left(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{OH}\right)\).
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