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Chapter 24: Problem 45

State which member of each of the following pairs of compounds is the more reactive and explain why: (a) propane and cyclopropane, (b) ethylene and methane, (c) acetaldehyde and acetone.

Short Answer

Expert verified
The more reactive compound in each pair is: (a) cyclopropane due to its strained structure, (b) ethylene due to its double bonds, and (c) acetaldehyde because its carbonyl group is more accessible for attack.

Step by step solution

01

Compare Propane and Cyclopropane

Propane is a simple alkane with three carbon atoms, whereas cyclopropane is a cyclic alkane. The difference lies in the bond angles. In propane, the bond angles are close to the ideal 109.5 degrees (the tetrahedral angle). However, in cyclopropane, the bond angles are forced to be 60 degrees due to the cyclic structure, creating strain and making the molecule unstable. Reactivity is directly proportional to instability, hence cyclopropane is more reactive.
02

Compare ethylene and methane

Ethylene, also known as ethene, is an alkene, which means it has a double bond between its two carbon atoms. Methane, on the other hand, is an alkane, meaning it only has single bonds. In general, double bonds are more reactive than single bonds because they can break more easily, meaning ethylene is more reactive.
03

Compare acetaldehyde and acetone

Acetaldehyde and acetone both have a carbonyl group, but in acetaldehyde, the carbonyl group is on an end carbon (making it an aldehyde), while in acetone, it is on a middle carbon (making it a ketone). Aldehydes are generally more reactive than ketones because the carbonyl carbon in aldehydes only has one alkyl group attached, leaving it more open to attack by nucleophiles. Hence acetaldehyde is more reactive.

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Most popular questions from this chapter

A compound has the empirical formula \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\). Upon controlled oxidation, it is converted into a compound of empirical formula \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O},\) which behaves as a ketone. Draw possible structures for the original compound and the final compound.

State at least one commercial use for each of the following compounds: (a) 2 -propanol (isopropanol), (b) acetic acid, (c) naphthalene, (d) methanol, (e) ethanol, (f) ethylene glycol, (g) methane, (h) ethylene.

How many distinct chloropentanes, \(\mathrm{C}_{5} \mathrm{H}_{11} \mathrm{Cl}\), could be produced in the direct chlorination of \(n\) -pentane, \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{3} \mathrm{CH}_{3} ?\) Draw the structure of each molecule.

Identify the functional groups in each of the following molecules: (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{COOC}_{2} \mathrm{H}_{5}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\)

Comment on the extra stability of benzene compared to ethylene. Why does ethylene undergo addition reactions while benzene usually undergoes substitution reactions?
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