Question

${\mathrm{CH}}_2=\mathrm{C}=\mathrm{O}+{\mathrm{I}}_2⟶\mathrm{P}\stackrel{{\mathrm{H}}_2\mathrm{O}}{⟶}\mathrm{Q};$ The product ' $\mathrm{Q}$ ' is (A) O=CCCO (B) O=C(O)CO (C) O=C(O)CI (D)

Short answer

The product Q is (C) $⟨\text{smiles}⟩$O=C(O)CI$⟨\text{/smiles}⟩$.

Step-by-step solution

Reaction of CH2=C=O with I2

Add iodine(I2) across the double bond of CH2=C=O. The structure of product P will have iodine atoms connected to the carbon atoms where the double bond was present.

Determining the structure of product P

The product P has the following structure: CH2I-CI=O

Analyzing the Reaction of P with H2O

Now, we need to perform hydrolysis of P by adding water (H2O) across the -CI=O bond. This process will replace the =O bond with an -OH group and remove the iodine.

Determining the structure of product Q

After hydrolysis, the final product Q will have the following structure: CH2I-C(OH)=O Now, let's match our result with the given options: (A) O=CCCO (B) O=C(O)CO (C) O=C(O)CI (D) The correct answer is (C).

Key concepts

Hydrolysis

Hydrolysis is a fundamental chemical process often encountered in organic chemistry reactions. It involves the breaking of bonds in a molecule using water. In the exercise problem, hydrolysis occurs when product P, originally derived from iodine addition to a carbon-oxygen double bond, reacts with water. Let's break down how this process works.

• Hydrolysis typically involves nucleophilic attack of water or hydroxide ions. This means that the water molecule will donate a pair of electrons to form a bond with a positively charged or electron-deficient atom.
• This addition of water to the chemical structure effectively cleaves a bond, leading to the formation of two separate compounds or the modification of the existing one.
• In this specific reaction, water adds to the carbon-iodine double bond, replacing the iodine with an -OH group, leading to the formation of a carboxylic acid derivative, as given in the exercise solution.

Understanding hydrolysis helps reveal the versatility and adaptability of chemical reactions in organic chemistry. By mastering this concept, you can predict reaction outcomes and better understand molecular transformations.

Reaction Mechanism

A reaction mechanism describes the step-by-step sequence through which a chemical reaction occurs. Each step provides details on how reactants are transformed into products, which is crucial for understanding reaction dynamics.

• In the case of the reaction discussed in the exercise, the mechanism begins with the addition of iodine ( I_2 ) to a double bond present in the starting material ( CH_2=C=O ). This action forms an initial intermediate (Product P).
• Next, hydrolysis occurs, where water reacts with Product P, replacing the iodine, resulting in the final product (Product Q).
• Each step has its own "mechanism" at the molecular level, involving the breaking and formation of specific chemical bonds.

Understanding reaction mechanisms allows chemists to predict which products will form, understand possible side reactions, and design new reactions. It is akin to reading the roadmap of a chemical conversion, ensuring you reach your desired destination.

Structure Determination

Structure determination is a critical step in organic chemistry to figure out how atoms are connected within a molecule. It ties together information from the reaction mechanism and hydrolysis process to verify the final product claimed in the solution.

• This involves identifying the specific bonds and connectivity in the compound after transformation, such as using spectroscopic methods in practice, but often through deduction in textbook scenarios.
• In the given exercise, structure determination of product Q involves checking the rearranged structure for product P after hydrolysis.
• The step-by-step analysis confirms product Q to be O=C(O)CI , which matches option (C) provided in the solutions.

Mastery of structure determination enables chemists to validate the hypothesized outcomes of reactions. It is like the final proofreading of a reaction’s result, ensuring that the intended molecular "sentence" has been properly constructed.