Draw The Structural Formula Of 3Z 5Z 4 5-Dimethyl-3 5-Nonadiene

Embarking on an exploration of Draw The Structural Formula Of 3Z 5Z 4 5-Dimethyl-3 5-Nonadiene, this discourse delves into the intricacies of its molecular structure, properties, synthesis, reactivity, and potential applications. Prepare to unravel the fascinating world of organic chemistry as we dissect this compound’s unique characteristics.

3Z 5Z 4 5-Dimethyl-3 5-Nonadiene, an organic compound belonging to the class of alkenes, possesses a captivating molecular architecture. Its structural formula, meticulously crafted using IUPAC nomenclature, unveils a chain of nine carbon atoms adorned with two double bonds at specific positions.

This precise arrangement of atoms imparts distinct physical and chemical properties to the molecule, shaping its behavior and reactivity.

Structural Formula

The structural formula of 3Z,5Z-4,5-dimethyl-3,5-nonadiene is as follows:

CH ₃CH ₂CH=CHCH(CH ₃)CH=CHCH ₂CH ₃

IUPAC Naming Convention

According to the IUPAC naming convention, the name of this compound is derived from the following rules:

• The base chain is a nine-carbon chain, which is named “nonane”.
• There are two double bonds in the molecule, located at the third and fifth carbons. The “Z” designation indicates that the two methyl groups on each double bond are on the same side of the double bond.
• The methyl groups are located at the fourth and fifth carbons, so the name is “4,5-dimethyl”.

Putting all of these together, the IUPAC name of the compound is 3Z,5Z-4,5-dimethyl-3,5-nonadiene.

Molecular Properties

3Z,5Z-4,5-dimethyl-3,5-nonadiene possesses unique physical and chemical properties due to the presence of its two double bonds.

The double bonds introduce rigidity into the molecular structure, restricting rotation around the carbon-carbon bonds. This rigidity affects the molecule’s shape, reactivity, and intermolecular interactions.

Physical Properties

• Boiling Point:The presence of the double bonds elevates the boiling point compared to alkanes of similar molecular weight. The double bonds restrict molecular motion, increasing the intermolecular forces and the energy required to overcome them during vaporization.
• Melting Point:The double bonds hinder close packing of molecules, resulting in a lower melting point compared to alkanes. The restricted molecular motion reduces the intermolecular forces, making it easier for the molecules to overcome these forces and transition from a solid to a liquid state.

• Density:The presence of the double bonds generally decreases the density of the molecule. The double bonds create steric hindrance, preventing molecules from packing closely together, resulting in a lower density.

Chemical Properties

• Reactivity:The double bonds in 3Z,5Z-4,5-dimethyl-3,5-nonadiene are susceptible to electrophilic addition reactions. The electron-rich double bonds react with electrophiles, such as hydrogen ions (H+) or bromine (Br2), to form addition products.
• Polymerization:Under appropriate conditions, 3Z,5Z-4,5-dimethyl-3,5-nonadiene can undergo polymerization reactions. The double bonds can react with each other to form polymers, which are long chains of repeating units.

Synthesis

3Z,5Z-4,5-dimethyl-3,5-nonadiene can be synthesized through various methods, each with its own advantages and disadvantages.

Wittig Reaction

The Wittig reaction involves the reaction of a phosphonium ylide with a carbonyl compound to form an alkene. In the case of 3Z,5Z-4,5-dimethyl-3,5-nonadiene, the starting materials would be 3-methyl-2-butanone and (Z)-2-bromo-2-butene. The reaction proceeds via a nucleophilic attack of the ylide on the carbonyl carbon, followed by elimination of triphenylphosphine oxide.

The Z-stereochemistry of the double bonds is controlled by the use of a bulky base, such as potassium tert-butoxide.

Advantages:

• Mild reaction conditions
• High yields
• Stereoselective

Disadvantages:

• Requires the use of specialized reagents
• Can be sensitive to air and moisture

Tebbe Reaction

The Tebbe reaction is a titanium-mediated coupling reaction that can be used to form alkenes from aldehydes or ketones. In the case of 3Z,5Z-4,5-dimethyl-3,5-nonadiene, the starting materials would be 3-methyl-2-butanone and 1-butene. The reaction proceeds via the formation of a titanium complex, which undergoes a series of insertions and eliminations to form the desired alkene.

The Z-stereochemistry of the double bonds is controlled by the use of a chiral ligand.

Advantages:

• Mild reaction conditions
• High yields
• Stereoselective

Disadvantages:

• Requires the use of specialized reagents
• Can be sensitive to air and moisture

Julia-Lythgoe Olefination

The Julia-Lythgoe olefination is a sulfone-based method for the synthesis of alkenes. In the case of 3Z,5Z-4,5-dimethyl-3,5-nonadiene, the starting materials would be 3-methyl-2-butanone and (Z)-2-bromo-2-butene. The reaction proceeds via the formation of a sulfone intermediate, which undergoes a series of eliminations to form the desired alkene.

The Z-stereochemistry of the double bonds is controlled by the use of a bulky base, such as potassium tert-butoxide.

Advantages:

• Mild reaction conditions
• High yields
• Stereoselective

Disadvantages:

• Requires the use of specialized reagents
• Can be sensitive to air and moisture

Reactivity: Draw The Structural Formula Of 3Z 5Z 4 5-Dimethyl-3 5-Nonadiene

Z,5Z-4,5-dimethyl-3,5-nonadiene is a highly reactive compound due to the presence of two double bonds in its structure. These double bonds make the compound susceptible to a variety of chemical reactions, including addition, oxidation, and polymerization reactions.

Addition Reactions

Z,5Z-4,5-dimethyl-3,5-nonadiene can undergo addition reactions with a variety of reagents, including hydrogen, halogens, and water. In these reactions, the double bonds are broken and new bonds are formed between the carbon atoms of the double bond and the atoms of the reagent.For

example, when 3Z,5Z-4,5-dimethyl-3,5-nonadiene is reacted with hydrogen in the presence of a catalyst, the double bonds are hydrogenated and the product is 4,5-dimethylnonane.“`

Z,5Z-4,5-dimethyl-3,5-nonadiene + H2 → 4,5-dimethylnonane

“`Similarly, when 3Z,5Z-4,5-dimethyl-3,5-nonadiene is reacted with bromine, the double bonds are brominated and the product is 4,5-dibromo-4,5-dimethylnonane.“`

Z,5Z-4,5-dimethyl-3,5-nonadiene + Br2 → 4,5-dibromo-4,5-dimethylnonane

“`

Oxidation Reactions

Z,5Z-4,5-dimethyl-3,5-nonadiene can also undergo oxidation reactions with a variety of reagents, including oxygen, potassium permanganate, and ozone. In these reactions, the double bonds are oxidized and the products are various oxygenated compounds, such as epoxides, aldehydes, and ketones.For example, when 3Z,5Z-4,5-dimethyl-3,5-nonadiene is reacted with ozone, the double bonds are ozonized and the product is 4,5-dimethyl-1,2,3-trioxolane.“`

Z,5Z-4,5-dimethyl-3,5-nonadiene + O3 → 4,5-dimethyl-1,2,3-trioxolane

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Polymerization Reactions

Z,5Z-4,5-dimethyl-3,5-nonadiene can also undergo polymerization reactions with a variety of catalysts, including Ziegler-Natta catalysts and metallocene catalysts. In these reactions, the double bonds are polymerized and the product is a high-molecular-weight polymer.For example, when 3Z,5Z-4,5-dimethyl-3,5-nonadiene is reacted with a Ziegler-Natta catalyst, the double bonds are polymerized and the product is a high-molecular-weight poly(4,5-dimethyl-3,5-nonadiene).“`n

3Z,5Z-4,5-dimethyl-3,5-nonadiene → poly(4,5-dimethyl-3,5-nonadiene)“`

Applications

3Z,5Z-4,5-dimethyl-3,5-nonadiene possesses unique properties that make it suitable for various applications across diverse fields.

Its high reactivity and ability to undergo a wide range of chemical reactions make it a valuable intermediate in the synthesis of more complex compounds. The presence of the two conjugated double bonds enhances its reactivity, enabling it to participate in reactions such as cycloadditions, Diels-Alder reactions, and metathesis.

Polymerization

3Z,5Z-4,5-dimethyl-3,5-nonadiene is used as a monomer in the production of polymers. Its conjugated double bonds allow it to undergo polymerization reactions, leading to the formation of polymers with alternating single and double bonds. These polymers exhibit unique properties, such as high strength, flexibility, and thermal stability.

Fragrance Industry

3Z,5Z-4,5-dimethyl-3,5-nonadiene is employed in the fragrance industry as a fragrance ingredient. Its distinct aroma makes it a popular choice for creating floral, fruity, and citrusy scents. The presence of the conjugated double bonds contributes to its pleasant odor and enhances its stability in fragrance formulations.

Pharmaceuticals, Draw The Structural Formula Of 3Z 5Z 4 5-Dimethyl-3 5-Nonadiene

3Z,5Z-4,5-dimethyl-3,5-nonadiene has potential applications in the pharmaceutical industry. Its structural features, including the conjugated double bonds and the presence of methyl groups, make it a promising candidate for drug development. Further research is needed to explore its therapeutic potential and identify specific applications.

Final Review

In conclusion, our journey into the realm of Draw The Structural Formula Of 3Z 5Z 4 5-Dimethyl-3 5-Nonadiene has illuminated its intricate molecular structure, diverse properties, and potential applications. This compound stands as a testament to the power of chemistry, showcasing how the arrangement of atoms can give rise to a molecule with unique characteristics and practical significance.

As we bid farewell to this exploration, we are left with a deeper appreciation for the complexities of organic chemistry and the endless possibilities it holds for scientific discovery and technological advancements.