Predict the products of the reactions of the following compounds with:
1. chromic acid or excess sodium hypochlorite with acetic acid.
2. PCC or NaOCl (1 equivalent) with TEMPO.
f. 1-phenylpropan-1-ol

Verified step by step guidance

1. Step 1: Identify the functional group in 1-phenylpropan-1-ol. The compound contains a primary alcohol (-OH group) attached to a carbon that is part of a propyl chain, which is also connected to a phenyl group (C6H5).
2. Step 2: Analyze the reaction conditions for (1) chromic acid (H2CrO4) or excess sodium hypochlorite (NaOCl) with acetic acid. Both are strong oxidizing agents that can oxidize primary alcohols to carboxylic acids. The reaction proceeds through the intermediate formation of an aldehyde, which is further oxidized to a carboxylic acid.
3. Step 3: Predict the product for reaction (1). The primary alcohol group (-CH2OH) in 1-phenylpropan-1-ol will be oxidized to a carboxylic acid group (-COOH), resulting in the formation of 1-phenylpropanoic acid.
4. Step 4: Analyze the reaction conditions for (2) PCC (pyridinium chlorochromate) or NaOCl (1 equivalent) with TEMPO. These are milder oxidizing agents that selectively oxidize primary alcohols to aldehydes without further oxidation to carboxylic acids.
5. Step 5: Predict the product for reaction (2). The primary alcohol group (-CH2OH) in 1-phenylpropan-1-ol will be oxidized to an aldehyde group (-CHO), resulting in the formation of 1-phenylpropanal.

Key Concepts

Oxidation Reactions

Oxidation reactions involve the loss of electrons or an increase in oxidation state of a molecule. In organic chemistry, this often pertains to the conversion of alcohols to carbonyl compounds (aldehydes or ketones) or further to carboxylic acids. Understanding the specific oxidizing agents, such as chromic acid or sodium hypochlorite, is crucial for predicting the products of these reactions.

Oxidizing Agents

Oxidizing agents are substances that facilitate the oxidation of other compounds by accepting electrons. Chromic acid and sodium hypochlorite are strong oxidizers that can convert primary alcohols to carboxylic acids or secondary alcohols to ketones. The choice of oxidizing agent and its conditions (excess or limited) significantly influence the reaction pathway and final products.

Selective Oxidation

Selective oxidation refers to the ability to oxidize specific functional groups in a molecule without affecting others. For instance, using PCC (Pyridinium chlorochromate) or NaOCl in the presence of TEMPO allows for the selective oxidation of alcohols to aldehydes or ketones, minimizing over-oxidation. This concept is essential for predicting the outcomes of reactions involving complex organic molecules.