Chapter 21

What is the difference between the hybridization of carbon atoms’ valence orbitals in saturated and unsaturated hydrocarbons?

Explain why unbranched alkenes can form geometric isomers while unbranched alkanes cannot. Does this explanation involve the macroscopic domain or the microscopic domain?

Write the Lewis structure and molecular formula for each of the following hydrocarbons: (a) hexane (b) 3-methylpentane (c) cis-3-hexene (d) 4-methyl-1-pentene (e) 3-hexyne (f) 4-methyl-2-pentyne

Write the chemical formula, condensed formula, and Lewis structure for each of the following hydrocarbons: (a) heptane (b) 3-methylhexane (c) trans-3-heptene (d) 4-methyl-1-hexene (e) 2 -heptyne (f) 3,4-dimethyl-1-pentyne

Write Lewis structures and name the five structural isomers of hexane.

Write Lewis structures for the cis-trans isomers of \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCl}\)

Write structures for the three isomers of the aromatic hydrocarbon xylene, \(\mathrm{C}_{6} \mathrm{H}_{4}\left(\mathrm{CH}_{3}\right)_{2}\)

Write Lewis structures and IUPAC names for the alkyne isomers of \(\mathrm{C}_{4} \mathrm{H}_{6}\)

Write the structures for all the isomers of the \(-\mathrm{C}_{5} \mathrm{H}_{11}\) alkyl group.

Write Lewis structures and describe the molecular geometry at each carbon atom in the following compounds: (a) cis-3-hexene (b) cis-1-chloro-2-bromoethene (c) 2 -pentyne (d) trans- 6 -ethyl- 7 -methyl- 2 -octene

Benzene is one of the compounds used as an octane enhancer in unleaded gasoline. It is manufactured by the catalytic conversion of acetylene to benzene: \(3 \mathrm{C}_{2} \mathrm{H}_{2} \longrightarrow \mathrm{C}_{6} \mathrm{H}_{6}\) Draw Lewis structures for these compounds, with resonance structures as appropriate, and determine the hybridization of the carbon atoms in each.

What mass of 2 -bromopropane could be prepared from \(25.5 \mathrm{g}\) of propene? Assume a \(100 \%\) yield of product.

Ethylene can be produced by the pyrolysis of ethane: \(\mathrm{C}_{2} \mathrm{H}_{6} \longrightarrow \mathrm{C}_{2} \mathrm{H}_{4}+\mathrm{H}_{2}\) How many kilograms of ethylene is produced by the pyrolysis of \(1.000 \times 10^{3} \mathrm{kg}\) of ethane, assuming a \(100.0 \%\) yield?

Why do the compounds hexane, hexanol, and hexene have such similar names?

Write condensed formulas and provide IUPAC names for the following compounds: (a) ethyl alcohol (in beverages) (b) methyl alcohol (used as a solvent, for example, in shellac) (c) ethylene glycol (antifreeze) (d) isopropyl alcohol (used in rubbing alcohol) (e) glycerine

Write the condensed structures of both isomers with the formula \(\mathrm{C}_{2} \mathrm{H}_{6}\) O. Label the functional group of each isomer.

Write the condensed structures of all isomers with the formula \(\mathrm{C}_{2} \mathrm{H}_{6} \mathrm{O}_{2}\). Label the functional group (or groups) of each isomer.

Draw the condensed formulas for each of the following compounds: (a) dipropyl ether (b) 2,2-dimethyl-3-hexanol (c) 2 -ethoxybutane

Explain why it is not possible to prepare a ketone that contains only two carbon atoms.

Fatty acids are carboxylic acids that have long hydrocarbon chains attached to a carboxylate group. How does a saturated fatty acid differ from an unsaturated fatty acid? How are they similar?

Write a condensed structural formula, such as \(\mathrm{CH}_{3} \mathrm{CH}_{3}\), and describe the molecular geometry at each carbon atom. (a) propene (b) 1-butanol (c) ethyl propyl ether (d) cis-4-bromo-2-heptene (e) 2,2,3 -trimethylhexane (f) formaldehyde

Write a condensed structural formula, such as \(\mathrm{CH}_{3} \mathrm{CH}_{3}\), and describe the molecular geometry at each carbon atom. (a) 2 -propanol (b) acetone (c) dimethyl ether (d) acetic acid (e) 3-methyl-1-hexene

The foul odor of rancid butter is caused by butyric acid, \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}\) (a) Draw the Lewis structure and determine the oxidation number and hybridization for each carbon atom in the molecule. (b) The esters formed from butyric acid are pleasant-smelling compounds found in fruits and used in perfumes. Draw the Lewis structure for the ester formed from the reaction of butyric acid with 2 -propanol.

Write the two-resonance structures for the acetate ion.

What is the molecular structure about the nitrogen atom in trimethyl amine and in the trimethyl ammonium ion, \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{NH}^{+} ?\) What is the hybridization of the nitrogen atom in trimethyl amine and in the trimethyl ammonium ion?

Write the two resonance structures for the pyridinium ion, \(\mathrm{C}_{5} \mathrm{H}_{5} \mathrm{NH}^{+}\)

Draw Lewis structures for pyridine and its conjugate acid, the pyridinium ion, \(\mathrm{C}_{5} \mathrm{H}_{5} \mathrm{NH}^{+}\). What are the geometries and hybridizations about the nitrogen atoms in pyridine and in the pyridinium ion?