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\(\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{Cl} \stackrel{\mathrm{OH}^{-}, \mathrm{Cl}_{2}}{\longrightarrow}\) Product \(\mathrm{P}\) is (a) \(\mathrm{ClCH}_{2} \mathrm{COCH}_{2} \mathrm{Cl}\) (b) \(\mathrm{CH}_{3} \mathrm{COCHCl}_{2}\) (c) Both (a) and (b) (d) \(\mathrm{ClCH}_{2} \mathrm{COOH}+\mathrm{CH}_{3} \mathrm{Cl}\)

Short Answer

Expert verified
The product \( \mathrm{P} \) is \( \mathrm{CH}_{3} \mathrm{COCHCl}_{2} \) (option b).

Step by step solution

01

Understand the Reaction Components

The given reaction involves the compound \( \mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{Cl} \) subject to hydroxide ion (\( \mathrm{OH}^{-} \)) and chlorine (\( \mathrm{Cl}_{2} \)). The goal is to determine the resultant product \( \mathrm{P} \).
02

React \( \mathrm{OH}^{-} \) with the Compound

The first reaction condition involves a hydroxide ion \( \mathrm{OH}^{-} \). Hydroxide typically acts as a basic and nucleophilic reagent which can initiate nucleophilic substitution at sites susceptible to displacement like \( \mathrm{C} \)-\mathrm{Cl} bonds, yielding \( \mathrm{CH}_{2} \mathrm{COCH}_{2} \mathrm{OH} \).
03

Determine Reaction with \( \mathrm{Cl}_{2} \)

The presence of \( \mathrm{Cl}_{2} \) can lead to chlorination. Chlorine can substitute or add to reactive sites, particularly at the \( \alpha \)-carbon (carbon next to the carbonyl group) resulting in the formation of \( \mathrm{CH}_{3} \mathrm{COCHCl}_{2} \).
04

Analyze the Possible Products

Comparing the final product from the reactions to the given options, Option (b) \( \mathrm{CH}_{3} \mathrm{COCHCl}_{2} \) matches, as \( \mathrm{Cl}_{2} \) adds to the \( \alpha \)-hydrogens, forming a dichloro compound.

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Key Concepts

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

Nucleophilic Substitution
In organic chemistry, nucleophilic substitution is an essential reaction where a nucleophile replaces a leaving group in a molecule. A nucleophile is a species rich in electrons and can donate an electron pair, while the leaving group is the atom or group that departs with an electron pair.
In the given reaction, the hydroxide ion (\(\mathrm{OH}^{-}\)) acts as the nucleophile. Hydroxide ions are particularly good nucleophiles because of their negative charge and availability of lone pair electrons.
A common site for nucleophilic substitution is the carbon-halogen bond (\(\mathrm{C-Cl}\)). The bond between carbon and chlorine is polarized, with chlorine being the more electronegative element. This polarization makes the carbon atom an ideal target for nucleophilic attack, leading to the displacement of the chlorine atom.
  • In this reaction, the hydroxide ion attacks the carbon bonded to chlorine in \(\mathrm{CH_{3}COCH_{2}Cl}\), replacing the chlorine and forming \(\mathrm{CH_{3}COCH_{2}OH}\). This reaction evidences the concept of nucleophilic substitution, where one atom is replaced by another more electron-rich atom or group.
Chlorination
Chlorination in organic chemistry involves introducing chlorine atoms into a molecular compound. This reaction is crucial in the formation of chlorinated hydrocarbons.
The active \(\mathrm{Cl_{2}}\) molecule can add to various positions in a molecule, particularly at those readily reactive or electron-rich sites.
In this exercise, chlorination occurs at the \(\alpha\)-carbon, which is the carbon directly adjacent to the carbonyl group. The particular significance of the \(\alpha\)-carbon originates from its higher acidity compared to other hydrogen atoms in the molecule, making \(\alpha\)-hydrogens more likely to participate in reactions.
  • For example, here, the \(\mathrm{Cl_{2}}\) reacts with the \(\alpha\)-hydrogens of \(\mathrm{CH_{3}COCH_{2}OH}\), resulting in the replacement of \(\alpha\)-hydrogens by chlorine. This leads to the formation of \(\mathrm{CH_{3}COCHCl_{2}}\). This step of adding chlorine substitutes the \(\alpha\)-hydrogens, leading to a dichloro compound.
Alpha Carbon
The \(\alpha\)-carbon is a prominent feature in organic chemistry due to its involvement in various reactions. Located next to a carbonyl carbon (carbon double-bonded to oxygen), it bears special properties influencing its reactivity.
The \(\alpha\)-hydrogens are relatively more acidic, allowing reactions like deprotonation to occur more readily. This acidity arises from the resonance stabilization provided by the carbonyl group, which can distribute the negative charge after hydrogen loss.
  • In chlorination reactions, the increased acidity of \(\alpha\)-hydrogens also facilitates halogenation upon exposure to chlorine. This helps in the substitution at the \(\alpha\)-carbon, transforming the molecular structure by replacing hydrogen with a halogen such as chlorine.
    Thus, in the given reaction, the role of the \(\alpha\)-carbon is pivotal, as it directs and facilitates the chlorination process, resulting in \(\mathrm{CH_{3}COCHCl_{2}}\), where the added chlorine atoms modify the original compound structure.

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Most popular questions from this chapter

When the following three different types of esters are hydrolyzed in a basic medium, the hydroxide anion attacks the acyl carbon in carboxylates while it attacks the alkyl carbon in sulphonates leading to a difference in the site of cleavage. More interestingly, phosphate esters lie somewhat in between carboxylates and sulphonates in that cleavage can occur in either direction. In an acidic solution, all the three types of phosphates (monoalkyl, dialkyl and trialkyl) are hydrolyzed to phosphoric acid, while in a basic solution only trialkyl phosphates undergo hydrolysis and only one alkoxy group is removed. Which of the following factor explains the difference in attack of the nucleophile, \(\mathrm{OH}^{-}\) on carboxylates and sulphonates? (a) Sulphonate anions are weakly basic and hence good leaving groups. (b) Carboxylate anions are strongly basic and hence poor leaving groups. (c) Both (a) and (b) (d) None of the these

Which of the following statements is true? (a) Hydrogen bonding always increases the acidic character of a species. (b) Hydrogen bonding always decreases the acidic character of a species. (c) Hydrogen bonding may increase or decrease the acidic character of a species. (d) Hydrogen bonding play no role in determining the acidity of a species.

Methanoic acid, the first member of carboxylic acid series, when warmed with concentrated sulphuric acid decompose in the following way and evolve carbon monoxide The driving force for this reaction lies in the fact that the \(\mathrm{HC} \equiv \mathrm{O}^{+}\) ion is very unstable acid and thus easily loses \(\mathrm{H}^{+}\). If acetic acid is replaced by triphenylacetic acid, the product formed will be (a) \(\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \mathrm{CH}+\mathrm{CO}\) (b) \(\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \mathrm{CH}+\mathrm{CO}_{2}\) (c) \(\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{3} \mathrm{COH}+\mathrm{CO}\) (d) No reaction

Products \(\left(\mathrm{P}_{2}\right)\) \(\stackrel{\text { anhy. } \mathrm{HI}}{\longleftarrow}\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{O}-\mathrm{CH}_{3} \stackrel{\text { Conc. } \mathrm{HI}}{\longrightarrow}\) Products \(\left(\mathrm{P}_{1}\right)\) The products \(\mathrm{P}_{1}\) and \(\mathrm{P}_{2}\) respectively are (a) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}+\mathrm{CH}_{3} \mathrm{I}\) and \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CI}+\mathrm{CH}_{3} \mathrm{OH}\) (b) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CI}+\mathrm{CH}_{3} \mathrm{OH}\) and \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}+\mathrm{CH}_{3} \mathrm{I}\) (c) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CI}+\mathrm{CH}_{3} \mathrm{OH}\) in both cases (d) \(\mathrm{CH}_{3} \mathrm{I}\) and \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}\) in both cases

Which of the following statement is false? (a) Cannizzaro reaction is given by aldehydes in presence of alkali (b) Aldol condensation is given by aldehydes in presence of alkali (c) Aldol condensation is given by aldehydes and ketones in presence of acids (d) None of these

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