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Chapter 18: Problem 50

(a) Draw all the isomeric diaminodichlorobenzenes. (b) Name each one and indicate which are polar and which are nonpolar.

Short Answer

Expert verified
There are three isomeric diaminodichlorobenzenes: 1,2-diamino-3,4-dichlorobenzene (polar), 1,2-diamino-4,5-dichlorobenzene (polar), and 1,3-diamino-2,4-dichlorobenzene (nonpolar). Their polarity depends on the symmetry of the substituent's positions.

Step by step solution

01

Drawing the Benzene Ring

Begin by drawing the basic structure of benzene, a hexagonal ring with three double bonds alternating between single bonds.
02

Adding Substituents for Isomers

Create all possible isomers by placing two amino groups (NH2) and two chlorine atoms (Cl) at different positions on the benzene ring. Remember that the orientation can be ortho (adjacent), meta (separated by one carbon), or para (opposite each other) for each substituent.
03

Drawing Structural Isomers

First, identify the unique placements of Cl and NH2 groups on the benzene ring to ensure all isomers are accounted for. Draw each structural isomer with distinct positioning of these groups.
04

Naming the Isomers

Use IUPAC nomenclature to name each isomer based on the positions of the amino and chlorine groups on the benzene ring.
05

Determining Polarity of Each Isomer

Determine the molecular dipole moment based on the symmetry and the electronegativity of the amino and chlorine groups. Isomers with symmetric distribution will be nonpolar, whereas those with asymmetric distribution of these substituents will be polar.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Benzene Ring Structure
The benzene ring is a fundamental framework in organic chemistry, characterized by a six-carbon cyclic structure with alternating double and single bonds, also known as aromaticity.
  • Benzene has a planar hexagonal shape that imparts unique chemical stability due to resonating structures.
  • The delocalized electrons across the ring create a region of electron density, which can affect the reactivity of the molecule.
Understanding the benzene ring is crucial when exploring the properties and reactivity of aromatic compounds like diaminodichlorobenzenes.
IUPAC Nomenclature
The nomenclature of organic compounds is guided by a set of rules established by the International Union of Pure and Applied Chemistry (IUPAC).
  • To name benzene derivatives, the benzene ring is taken as the parent compound.
  • Substituent groups attached to the benzene ring are identified and used to derive the compound's name based on their relative positions.
For the isomers of diaminodichlorobenzenes, you'd typically number the ring to minimize the numerical sequence for substituents, using prefixes like 'ortho', 'meta', and 'para' to indicate the relative positions if only two types of substituents are present.
Molecular Polarity
Molecular polarity is a vector property arising from uneven distribution of electrons in a molecule.
  • Polarity affects properties like solubility, boiling point, and reactivity.
  • A molecular dipole moment is induced when there is an asymmetry in the electrical charge distribution, often due to electronegative atoms like chlorine.
For diaminodichlorobenzenes, the polarity will depend on how the Cl and NH2 groups are positioned relative to each other on the benzene ring.
Structural Isomers
Structural isomers are compounds with the same molecular formula but different arrangements of atoms.
  • In the context of diaminodichlorobenzenes, structural isomers vary based on the positions of the NH2 and Cl groups on the benzene ring.
  • Understanding different isomers is essential for predicting the physical and chemical behavior of a molecule.
Each isomer can exhibit distinct properties, making it critical to identify them accurately.
Ortho-meta-para Orientation
The ortho-meta-para terminology is specific to disubstituted benzene rings and refers to the relative positions of the substituents.
  • Ortho (o-) indicates that two substituents are adjacent, located at the 1 and 2 positions of the ring.
  • Meta (m-) describes substituents separated by one carbon atom, at the 1 and 3 positions.
  • Para (p-) refers to substituents directly across from each other, at the 1 and 4 positions.
The differing spatial arrangements resulting from these orientations can greatly affect the molecule's physical properties and reactivity.

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Most popular questions from this chapter

Identify each of the following pairs as structural isomers, geometrical isomers, or not isomers: (a) butane and cyclobutane; (b) cyclopentane and pentene; (a) (b)

Write the structural formulas for and name all the isomers (including geometrical isomers) of the alkenes (a) \(\mathrm{C}_{4} \mathrm{H}_{8}\); (b) \(\mathrm{C}_{5} \mathrm{H}_{10}\).

Predict the geometry and hybridization of the orbitals used in bonding on carbon atom 2 in (a) pentane; (b) 2-pentene; (c) 2-pentyne.

Draw the structures of cis-1,2-dichloropropene and trans1,2 -dichloropropene. Which of these molecules is polar?

The dehydrohalogenation of haloalkanes to produce alkenes is always carried out in a nonaqueous solvent, usually ethanol. Give two reasons why water cannot be used as the solvent for the reaction.
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