Chapter 26: Problem 44
Which of the following possesses highest melting point? (a) chlorobenzene (b) o-dichlorobenzene (c) \(\mathrm{m}\)-dichlorobenzene (d) \(\mathrm{p}\)-dichlorobenzene
Short Answer
Expert verified
p-Dichlorobenzene has the highest melting point.
Step by step solution
01
Understand the Structures
Identify the structure of each compound:
- Chlorobenzene has a benzene ring with one chlorine atom attached.
- o-Dichlorobenzene has two chlorine atoms attached to adjacent carbons on the benzene ring.
- m-Dichlorobenzene has two chlorine atoms with one carbon between them on the benzene ring.
- p-Dichlorobenzene has two chlorine atoms directly opposite each other on the benzene ring.
02
Analyze Molecular Symmetry
Consider the symmetry of each compound:
- p-Dichlorobenzene is the most symmetrical, with substitutions at opposite ends of the benzene ring.
- m-Dichlorobenzene and o-Dichlorobenzene have less symmetry, with chlorine atoms not directly opposing each other.
- Greater symmetry generally leads to more efficient packing in the solid state.
03
Determine Effect on Melting Point
Understand how symmetry affects melting points:
- More symmetric molecules tend to pack more tightly in the crystalline solid state, leading to higher melting points.
- p-Dichlorobenzene, being more symmetrical than the other options, will pack better in a solid state, leading to higher melting point than less symmetrical compounds.
04
Conclusion
Based on symmetry and packing, among the given options, g
delemparg)p-dichlorobenzene possesses the highest melting point due to its high symmetry and efficient packing in the solid state.
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Chlorobenzene
Chlorobenzene is a fascinating chemical compound often used in various industrial processes. It consists of a benzene ring, which is a six-carbon ring with alternating double bonds, forming a very stable structure. When one of these hydrogen atoms on benzene is replaced by a chlorine atom, chlorobenzene is created.
- Chlorobenzene retains the aromatic characteristics of benzene.
- The chlorine atom adds some interesting chemical properties due to its electronegativity.
- This results in distinct solubility and reactivity properties.
Molecular Symmetry
Molecular symmetry is a crucial concept in understanding the physical properties of substances, including their melting points. Symmetry in a molecule refers to the balanced distribution of its parts. When a molecule has a high degree of symmetry, its components can pack closely together in solid form, often resulting in a higher melting point.
- Symmetry helps molecules arrange themselves in more orderly, repeating patterns.
- This uniformity in structure allows for stronger intermolecular interactions.
- Greater interactions mean that more energy is needed to break the solid apart, implying a higher melting point.
Crystalline Structure
The crystalline structure of a compound is vital in determining its melting point and many other physical properties. Crystalline solids are characterized by a highly ordered and repeating arrangement of molecules.
- This order is due in part to the molecular symmetry of the substances involved.
- More symmetrical molecules contribute to forming more regular crystal lattices.
- These lattices are capable of withstanding high amounts of energy before the structure breaks apart during melting.