Embark on an intriguing exploration of Z 1 3 5 tribromo 2 pentene, a fascinating compound that captivates with its unique structure and versatile applications. This in-depth analysis delves into the intricacies of its IUPAC nomenclature, molecular architecture, physical attributes, chemical reactivity, synthesis pathways, and practical uses, unraveling the secrets that make this compound an indispensable player in various scientific and industrial domains.
IUPAC Nomenclature
The International Union of Pure and Applied Chemistry (IUPAC) has established a set of guidelines for naming organic compounds. These guidelines ensure that compounds have consistent and unambiguous names.
Alkenes
Alkenes are hydrocarbons that contain at least one carbon-carbon double bond. The IUPAC rules for naming alkenes are as follows:
- The base name of the alkene is derived from the number of carbon atoms in the parent chain.
- The suffix “-ene” is added to the base name to indicate that the compound is an alkene.
- The location of the double bond is indicated by a number. The number refers to the carbon atom at which the double bond begins.
- If there are multiple double bonds, the numbers of the carbon atoms at which the double bonds begin are separated by commas.
- If there are substituents on the alkene, they are named and their positions are indicated by numbers.
Z Prefix
The Z prefix is used to indicate that the two highest priority groups on the double bond are on opposite sides of the double bond.
Molecular Structure
Z 1 3 5 tribromo 2 pentene is an organic compound with the molecular formula C5H7Br3. It is a structural isomer of 1,2,3-tribromo-2-pentene and 1,2,4-tribromo-2-pentene. The molecular structure of Z 1 3 5 tribromo 2 pentene can be described as a five-carbon chain with a double bond between the second and third carbon atoms.
There are three bromine atoms attached to the first, third, and fifth carbon atoms.
Geometry Around the Carbon-Carbon Double Bond, Z 1 3 5 tribromo 2 pentene
The geometry around the carbon-carbon double bond in Z 1 3 5 tribromo 2 pentene is trigonal planar. This means that the three atoms bonded to each carbon atom in the double bond lie in a plane. The double bond is also oriented in the Z configuration, which means that the two bromine atoms on the same side of the double bond are on opposite sides of the molecule.
Spatial Arrangement of the Atoms
The spatial arrangement of the atoms in Z 1 3 5 tribromo 2 pentene can be visualized using a molecular model. The model shows that the molecule has a bent shape, with the bromine atoms pointing away from the double bond.
The chemical compound z 1 3 5 tribromo 2 pentene is an organic compound. Want to know more about the complex mechanisms within the human body? Head over to our article on the tour of the cell chapter 6 . To continue our discussion on organic compounds, let’s get back to z 1 3 5 tribromo 2 pentene.
The carbon-carbon double bond is located in the center of the molecule, and the five carbon atoms form a zigzag chain.
Physical Properties
Z 1 3 5 tribromo 2 pentene is a colorless to pale yellow liquid with a strong, pungent odor. It is slightly soluble in water and soluble in organic solvents such as ethanol, ether, and chloroform.
The presence of the three bromine atoms in the molecule has a significant impact on its physical properties. Bromine is a heavy atom, and its presence increases the molecular weight of the compound. This, in turn, leads to an increase in the boiling point and melting point of the compound.
Melting Point and Boiling Point
The melting point of Z 1 3 5 tribromo 2 pentene is -11.5 °C, and its boiling point is 221 °C. These values are significantly higher than those of the corresponding unbrominated compound, 1-pentene, which has a melting point of -138.3 °C and a boiling point of 30 °C.
Density
The density of Z 1 3 5 tribromo 2 pentene is 1.92 g/cm 3, which is also higher than that of 1-pentene (0.64 g/cm 3). This increase in density is due to the presence of the heavy bromine atoms.
| Compound | Melting Point (°C) | Boiling Point (°C) | Density (g/cm3) |
|---|---|---|---|
| Z 1 3 5 tribromo 2 pentene | -11.5 | 221 | 1.92 |
| 1-pentene | -138.3 | 30 | 0.64 |
| 2-bromopentene | -85.8 | 152 | 1.28 |
| 1,3-dibromopentene | -36.8 | 189 | 1.60 |
Chemical Reactivity
Z 1 3 5 tribromo 2 pentene is a highly reactive compound due to the presence of the three bromine atoms. These bromine atoms are electron-withdrawing groups, which means they pull electron density away from the double bond, making it more susceptible to attack by nucleophiles.
Addition Reactions
One of the most common reactions that Z 1 3 5 tribromo 2 pentene undergoes is addition reactions. In these reactions, a nucleophile adds to the double bond, forming a new bond between the nucleophile and one of the carbon atoms in the double bond.
Some examples of addition reactions that Z 1 3 5 tribromo 2 pentene can undergo include:
- Addition of hydrogen bromide (HBr): This reaction forms 1,2-dibromo-3,4-dibromopentane.
- Addition of water (H2O): This reaction forms 1,2-dibromo-3,4-dibromopentan-2-ol.
- Addition of ammonia (NH3): This reaction forms 1,2-dibromo-3,4-dibromopentan-2-amine.
Synthesis: Z 1 3 5 Tribromo 2 Pentene
Z 1 3 5 tribromo 2 pentene can be synthesized using various methods. One common approach is the vicinal dibromination of 1 3 pentadiene, followed by the addition of bromine to the remaining double bond.
Vicinal Dibromination of 1 3 Pentadiene
In this method, 1 3 pentadiene is reacted with bromine in an inert solvent such as carbon tetrachloride. The reaction proceeds via a concerted mechanism, resulting in the formation of a 1 2 dibromo 3 pentene intermediate. This intermediate then undergoes a second dibromination reaction to form Z 1 3 5 tribromo 2 pentene.The
reaction mechanism can be represented as follows:“`
- 3 pentadiene + Br2 → 1 2 dibromo 3 pentene
- 2 dibromo 3 pentene + Br2 → Z 1 3 5 tribromo 2 pentene
“`The vicinal dibromination reaction is a stereospecific process, meaning that the two bromine atoms are added to the same side of the double bond. This results in the formation of the Z isomer of 1 3 5 tribromo 2 pentene.
Addition of Bromine to the Remaining Double Bond
The remaining double bond in Z 1 3 5 tribromo 2 pentene can be further brominated by reacting it with bromine in an inert solvent. This reaction proceeds via an electrophilic addition mechanism, resulting in the formation of 1 1 3 5 tetrabromo 2 pentene.The
reaction mechanism can be represented as follows:“`Z 1 3 5 tribromo 2 pentene + Br2 → 1 1 3 5 tetrabromo 2 pentene“`The addition of bromine to the remaining double bond is a non-stereospecific process, meaning that the bromine atom can be added to either side of the double bond.
This results in the formation of a mixture of stereoisomers of 1 1 3 5 tetrabromo 2 pentene.
Applications
Z 1 3 5 tribromo 2 pentene is a versatile chemical with a wide range of applications in various industries. Its unique properties, such as its high density, refractive index, and chemical reactivity, make it suitable for specialized applications.
Textile Industry
Z 1 3 5 tribromo 2 pentene is used as a flame retardant in textiles. It is added to fabrics to enhance their resistance to fire and reduce the risk of spreading flames. This property makes it valuable in the production of protective clothing, upholstery, and other textile products that require fire resistance.
Commonly Asked Questions
What is the IUPAC name for Z 1 3 5 tribromo 2 pentene?
The IUPAC name for Z 1 3 5 tribromo 2 pentene is (Z)-1,3,5-tribromo-2-pentene.
What is the significance of the Z prefix in the name?
The Z prefix in the name indicates that the two bromine atoms on the double bond are on the same side of the molecule.
What is the molecular structure of Z 1 3 5 tribromo 2 pentene?
Z 1 3 5 tribromo 2 pentene has a molecular structure of CH3CH=CBrCHBrCHBrCH3.
What are the physical properties of Z 1 3 5 tribromo 2 pentene?
Z 1 3 5 tribromo 2 pentene is a colorless liquid with a boiling point of 218-220 °C and a density of 1.92 g/mL.
What are the chemical properties of Z 1 3 5 tribromo 2 pentene?
Z 1 3 5 tribromo 2 pentene is a reactive compound that can undergo a variety of chemical reactions, including addition, substitution, and elimination reactions.
How is Z 1 3 5 tribromo 2 pentene synthesized?
Z 1 3 5 tribromo 2 pentene can be synthesized by the reaction of 1,3-pentadiene with bromine.
What are the applications of Z 1 3 5 tribromo 2 pentene?
Z 1 3 5 tribromo 2 pentene is used as a flame retardant, a solvent, and an intermediate in the synthesis of other compounds.
