Question

Identify the product in the given reaction. \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}_{2}+\mathrm{NOCl} \rightarrow(\mathrm{A})\) (a) \(\mathrm{CH}_{3}-\mathrm{CHCl}-\mathrm{CH}_{2} \mathrm{NO}\) (b) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHClNO}\) (d) \(\mathrm{CH}_{3} \mathrm{NOCH}_{2} \mathrm{CH}_{2} \mathrm{Cl}\)

Short answer

Answer: The product of the reaction is CH3CH2CHClNO.

Step-by-step solution

Determine the reaction type

Since the reactants include an alkene and a molecule with a halogen (Cl), we can conclude that this is an addition reaction. In an addition reaction, the double bond of the alkene reacts with a molecule to form two new single bonds. Thus, the product will have a single bond between the two carbon atoms instead of the double bond in the alkene \(\mathrm{CH}_{3}\mathrm{CH}=\mathrm{CH}_{2}\).

Determine the outcome of the addition reaction

The reaction between the alkene and NOCl will proceed as a halogenation reaction, where the chlorine atom from NOCl will attach to one of the carbon atoms from the alkene double bond. Since this carbon-chlorine bond is more polar than a carbon-nitrogen bond, the nitrogen and oxygen atoms in NOCl will remain bonded together, and they will attach to the other carbon atom. This results in a product with the formula \(\mathrm{CH}_{3}\mathrm{CH}\mathrm{CH}_{2}\mathrm{ClNO}\).

Compare the given compounds to the expected product from step 2

We have determined that the product of the reaction should have the formula \(\mathrm{CH}_{3}\mathrm{CH}\mathrm{CH}_{2}\mathrm{ClNO}\). Comparing this formula to the given options, we can see that option (c) matches this formula.

Conclude

Therefore, the correct answer is option (c), as the product of the reaction between \(\mathrm{CH}_{3}\mathrm{CH}=\mathrm{CH}_{2}\) and \(\mathrm{NOCl}\) is \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHClNO}\).

Key concepts

Addition Reactions

Addition reactions are a cornerstone of organic chemistry, especially when dealing with unsaturated compounds like alkenes and alkynes. In an addition reaction, atoms or groups of atoms add across a double or triple bond. This process converts the multiple bonds into single bonds, thereby saturating the molecule.

Consider a simple alkene, such as propene, which is involved in the exercise. When propene \(\mathrm{CH}_3\mathrm{CH}=\mathrm{CH}_2\) reacts with another molecule, such as NOCl, the double bond allows the extra atoms to attach themselves more easily.

Key Features of Addition Reactions:

• Involves the conversion of \(\pi\) bonds to \(\sigma\) bonds.
• Usually results in two new \(\sigma\) bonds.
• Helps in transforming unsaturated compounds into saturated ones.

An addition reaction is a straightforward way of transforming alkenes. It forms the base of understanding more complex reaction mechanisms in organic chemistry.

Alkene Reactions

Alkenes are hydrocarbons that contain carbon-carbon double bonds (\(C=C\)). This makes them more reactive than alkanes, which only have single carbon-carbon bonds. The double bond is a region of high electron density, making it the ideal site for electrophiles to attack and form new bonds.

Let's break down how alkenes react in addition reactions:

Electrophilic Addition

• One of the two \(\pi\) electrons from the double bond is used to form a bond with the electrophile.
• This forms a carbocation, which can then react with nucleophiles.

In the exercise, the alkene propene reacts with NOCl. The double bond makes the central carbon electron-rich, serving as a perfect target for NOCl to attach.

Stability of the Carbocation

During the reaction process, a carbocation intermediate is often formed. Its stability greatly influences the final product. In this case, the propene's tertiary carbocation is more stable, favoring the formation of one specific product.

Halogenation

Halogenation is a specific type of addition reaction that involves the addition of halogen atoms to a molecule. In this process, a halogen molecule like \(Cl_2\) adds to the double bond of an alkene, converting it into a dihaloalkane.

In the given exercise, a less common version involving NOCl is used. Here's how it typically works:

• The double bond in the alkene attacks the halogen compound NOCl.
• The bond forms between the carbon of the double bond and the chlorine, creating a more polar C-Cl bond, whereas the other carbon bonds with the remaining NO group.

The result is a halogenated product with both chlorine and an NO group attached across the former double bond.

Halogenation reactions, especially those involving different reactants like NOCl, broaden the possibilities of synthesizing complex molecules. They are essential for creating building blocks in pharmaceuticals and materials science.