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Ch.11 - Reactions of Alcohols
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh.11 - Reactions of AlcoholsProblem 2g,h
Chapter 11, Problem 2g,h

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.
g. hexan-1-ol
h. acetaldehyde, CH3CHO

Verified step by step guidance
1
Step 1: Understand the reagents and their roles. Chromic acid (H2CrO4) and excess sodium hypochlorite (NaOCl) with acetic acid are strong oxidizing agents. PCC (Pyridinium Chlorochromate) and NaOCl with TEMPO are mild oxidizing agents. Strong oxidizing agents can fully oxidize primary alcohols to carboxylic acids, while mild oxidizing agents typically stop at aldehydes.
Step 2: Analyze the structure of hexan-1-ol (g). Hexan-1-ol is a primary alcohol. When treated with chromic acid or excess NaOCl with acetic acid, it will be oxidized to hexanoic acid (a carboxylic acid). When treated with PCC or NaOCl (1 equivalent) with TEMPO, it will be oxidized to hexanal (an aldehyde).
Step 3: Analyze the structure of acetaldehyde (h), CH3CHO. Acetaldehyde is already an aldehyde. Strong oxidizing agents like chromic acid or excess NaOCl with acetic acid will oxidize it further to acetic acid (CH3COOH). Mild oxidizing agents like PCC or NaOCl with TEMPO will not oxidize it further, as aldehydes are typically stable under mild conditions.
Step 4: Write the balanced chemical equations for each reaction. For hexan-1-ol with chromic acid: \( \text{C}_6\text{H}_{13}\text{OH} + H_2CrO_4 \rightarrow \text{C}_6\text{H}_{12}\text{COOH} \). For hexan-1-ol with PCC: \( \text{C}_6\text{H}_{13}\text{OH} + PCC \rightarrow \text{C}_6\text{H}_{12}\text{CHO} \). For acetaldehyde with chromic acid: \( \text{CH}_3\text{CHO} + H_2CrO_4 \rightarrow \text{CH}_3\text{COOH} \).
Step 5: Summarize the expected products. Hexan-1-ol reacts with strong oxidizing agents to form hexanoic acid and with mild oxidizing agents to form hexanal. Acetaldehyde reacts with strong oxidizing agents to form acetic acid but remains unchanged with mild oxidizing agents.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

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 aldehydes or ketones, and further to carboxylic acids. Understanding the specific oxidizing agents, such as chromic acid or PCC, is crucial as they dictate the extent of oxidation and the resulting products.
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Reactivity of Alcohols and Aldehydes

Alcohols and aldehydes exhibit distinct reactivity patterns due to their functional groups. Hexan-1-ol, a primary alcohol, can be oxidized to an aldehyde or carboxylic acid, while acetaldehyde can undergo further oxidation to acetic acid. Recognizing these transformations is essential for predicting the products of reactions with oxidizing agents.
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Role of Oxidizing Agents

Different oxidizing agents have varying strengths and selectivities. For instance, chromic acid is a strong oxidizer that can fully oxidize primary alcohols to carboxylic acids, while PCC is milder and typically oxidizes primary alcohols to aldehydes. Sodium hypochlorite (NaOCl) can also oxidize alcohols and aldehydes, but its reactivity can depend on the conditions and the presence of other reagents like TEMPO, which can influence the reaction pathway.
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Related Practice
Textbook Question

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.

d. cyclohexanone

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Textbook Question

We have covered several oxidants that use a multi-valent atom (Cr, Cl, S, or I) as their active species, going from a higher oxidation state before the oxidation to a lower oxidation state after oxidizing the alcohol. Draw the Lewis structures of the following atoms, before and after the oxidation of an alcohol to a ketone or aldehyde. How many bonds to oxygen does each atom have before and after the oxidation?

a. the Cr in chromic acid

b. the Cl in sodium hypochlorite

c. the S in the Swern oxidation

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Textbook Question

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.

e. cyclohexane

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Textbook Question

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

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Textbook Question

Give the structure of the principal product(s) when each of the following alcohols reacts with (3) DMP, and (4) 1 equiv NaOCl-TEMPO.

c. 4-hydroxydecanal

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Textbook Question

Give the structure of the principal product(s) when each of the following alcohols reacts with (1) Na2Cr2O7/H2SO4, (2) PCC, (3) DMP, and (4) 1 equiv NaOCl-TEMPO.

a. octan-1-ol

b. octan-3-ol

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