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Chapter 22: Problem 33

There is only one compound that is named 1,2 -dichloroethane, but there are two distinct compounds that can be named \(1,2-\) dichloroethene. Why?

Short Answer

Expert verified
The presence of a double bond in 1,2-dichloroethene allows it to exist in two different geometric forms: cis and trans isomers. These different spatial arrangements result in two distinct compounds with unique properties. On the other hand, 1,2-dichloroethane does not have any geometric isomer or conformer due to the absence of a double bond. Therefore, there is only one compound named 1,2-dichloroethane but two distinct compounds that can be named 1,2-dichloroethene.

Step by step solution

01

Understand the structure of 1,2-dichloroethane

The chemical formula for 1,2-dichloroethane is C2H4Cl2. The compound has two carbon (C) atoms, four hydrogen (H) atoms, and two chlorine (Cl) atoms. In the chemical structure, the two carbon atoms are bonded to each other with a single bond, and each carbon atom is bonded to two hydrogen atoms and one chlorine atom. Since the compound has only one type of arrangement, there is only one isomer or conformer, and thus, there is only one compound named 1,2-dichloroethane.
02

Understand the structure of 1,2-dichloroethene

The chemical formula for 1,2-dichloroethene is C2H2Cl2. The compound has two carbon (C) atoms, two hydrogen (H) atoms, and two chlorine (Cl) atoms. In the chemical structure, the two carbon atoms are bonded to each other with a double bond, and each carbon atom is bonded to one hydrogen atom and one chlorine atom. The presence of the double bond between carbon atoms makes it possible to have two distinct geometric arrangements for the compound, known as cis and trans isomers or conformers.
03

Understand the difference between cis and trans isomers in 1,2-dichloroethene

The cis and trans isomers in 1,2-dichloroethene have different spatial arrangements of their atoms. In the cis isomer, the two chlorine atoms are on the same side of the double bond, whereas in the trans isomer, the chlorine atoms are on opposite sides. This difference in spatial arrangement results in two distinct compounds with different physical and chemical properties.
04

Conclude why there are two distinct compounds for 1,2-dichloroethene and only one for 1,2-dichloroethane

The presence of a double bond in 1,2-dichloroethene allows it to exist in two different geometric forms: cis and trans isomers. These different spatial arrangements result in two distinct compounds with unique properties. On the other hand, 1,2-dichloroethane does not have any geometric isomer or conformer due to the absence of a double bond. Therefore, there is only one compound named 1,2-dichloroethane but two distinct compounds that can be named 1,2-dichloroethene.

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Key Concepts

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

Chemical Structure
Understanding the chemical structure of a compound is crucial in determining its characteristics and behaviors. Each molecule is composed of atoms bonded in specific ways, which dictates the overall shape and type of the compound.
An example is 1,2-dichloroethane, which has the chemical formula \( \text{C}_2\text{H}_4\text{Cl}_2 \).
Here, two carbon atoms are bonded with a single bond, each carbon also having two hydrogen and one chlorine bonded.
This simple configuration leads to a single possible arrangement, meaning there are no geometric isomers for 1,2-dichloroethane.
For 1,2-dichloroethene, however, the presence of a double bond changes the structural dynamics. Its formula \( \text{C}_2\text{H}_2\text{Cl}_2 \) involves two carbon atoms connected by a double bond, with each carbon attached to one hydrogen and one chlorine atom. This setup allows for different spatial arrangements, leading us to geometric isomers.
Double Bond
A double bond is a type of chemical bond where two pairs of electrons are shared between atoms. It is shorter and stronger than a single bond due to the sharing of more electrons, but it's also more rigid.
Because of its rigidity, compounds with double bonds, such as 1,2-dichloroethene, exhibit restricted rotation about the bond.
This restriction is what enables the existence of geometric isomers.
  • A single bond allows for free rotation, preventing different spatial arrangements.
  • A double bond's fixed nature means atoms cannot just rearrange freely around it.
In 1,2-dichloroethene, the double bond between the carbon atoms dictates the positioning of atoms, which gives rise to distinct geometric forms.
Cis-Trans Isomers
Cis-trans isomers, also known as geometric isomers, occur due to the limited rotation around the double bonds in molecules. This restriction results in different atom arrangements in space, even though the compositions are identical.
In chemistry, these isomers are termed based on the position of specific groups across the double bond:
  • **Cis Isomer:** Both chlorine atoms in 1,2-dichloroethene are on the same side of the double bond, leading to a specific molecular configuration.
  • **Trans Isomer:** The chlorine atoms are on opposite sides, creating a different configuration.
These configurations make each isomer have unique chemical and physical properties, such as boiling points or reactivity. Understanding cis and trans distinctions enhances our knowledge of how three-dimensional arrangements in space significantly influence molecular behavior.

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Most popular questions from this chapter

There are three isomers of dichlorobenzene, one of which has now replaced naphthalene as the main constituent of mothballs. a. Identify the ortho, the meta, and the para isomers of dichlorobenzene. b. Predict the number of isomers for trichlorobenzene. c. It turns out that the presence of one chlorine atom on a benzene ring will cause the next substituent to add ortho or para to the first chlorine atom on the benzene ring. What does this tell you about the synthesis of \(m\) -dichlorobenzene? d. Which of the isomers of trichlorobenzene will be the hardest to prepare?

Name all the aldehydes and ketones that have the formula \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O} .\)

For each of the following, fill in the blank with the correct response(s). All of the following pertain to nucleic acids. a. The substance in the nucleus of the cell that stores and transmits genetic information is DNA, which stands for b. The basic repeating monomer units of DNA and RNA are called c. The pentose deoxyribose is found in DNA, whereas is found in RNA. d. The basic linkage in DNA or RNA between the sugar molecule and phosphoric acid is a phosphate e. The bases on opposite strands of DNA are said to be to each other, which means the bases fit together specifically by hydrogen bonding to one another. f. In a strand of normal DNA, the base found paired with the base adenine, whereas is always found paired with cytosine. g. A given segment of the DNA molecule, which contains the molecular coding for a specific protein to be synthesized, is referred to as a- h. During protein synthesis, RNA molecules attach to and transport specific amino acids to the appropriate position on the pattern provided by RNA molecules. i. The codes specified by are responsible for assembling the correct primary structure of proteins.

Alcohols are very useful starting materials for the production of many different compounds. The following conversions, starting with 1-butanol, can be carried out in two or more steps. Show the steps (reactants/catalysts) you would follow to carry out the conversions, drawing the formula for the organic product in each step. For each step, a major product must be produced. See Exercise 62. (Hint: In the presence of \(\mathrm{H}^{+}\), an alcohol is converted into an alkene and water. This is the exact reverse of the reaction of adding water to an alkene to form an alcohol.) a. 1 -butanol \(\longrightarrow\) butane b. 1-butanol \(\longrightarrow 2\) -butanone

The codons (words) in DNA (that specify which amino acid should be at a particular point in a protein) are three bases long. How many such three- letter words can be made from the four bases adenine, cytosine, guanine, and thymine?
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