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Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
All textbooksMullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 106k(ix,x)
Chapter 12, Problem 106k(ix,x)

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (ix) PCC; (x) H2CrO4 , H2O If no reaction occurs, write 'no reaction.'


(k) Chemical structure of a cyclohexanol derivative with an attached hydroxyl group.

Verified step by step guidance
1
Identify the functional group in the molecule. The image shows a cyclohexane ring with a tertiary alcohol group attached.
Consider the reagents provided: PCC (Pyridinium Chlorochromate) and H₂CrO₄, H₂O. Both are oxidizing agents, but they have different strengths and selectivity.
Understand the action of PCC. PCC is a mild oxidizing agent that typically oxidizes primary alcohols to aldehydes and secondary alcohols to ketones. However, it does not oxidize tertiary alcohols.
Analyze the action of H₂CrO₄, H₂O. This is a strong oxidizing agent that can oxidize primary alcohols to carboxylic acids and secondary alcohols to ketones. Tertiary alcohols generally do not undergo oxidation with chromic acid because they lack a hydrogen atom on the carbon bearing the hydroxyl group.
Conclude that since the molecule contains a tertiary alcohol, neither PCC nor H₂CrO₄, H₂O will cause a reaction. Therefore, the result is 'no reaction.'

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Key Concepts

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

PCC (Pyridinium Chlorochromate)

PCC is a mild oxidizing agent commonly used in organic chemistry to convert primary alcohols to aldehydes and secondary alcohols to ketones without over-oxidation. It is preferred for its ability to selectively oxidize alcohols while minimizing further oxidation to carboxylic acids, making it useful in synthetic pathways where specific functional groups need to be preserved.
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Strong oxidizing agents

H₂CrO₄ (Chromic Acid)

H₂CrO₄ is a strong oxidizing agent that can oxidize primary alcohols to carboxylic acids and secondary alcohols to ketones. It is more aggressive than PCC and can lead to over-oxidation, which is important to consider when predicting reaction products. Understanding its reactivity helps in determining the outcome of reactions involving alcohols and other functional groups.
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Oxidation States and Functional Group Transformations

In organic chemistry, oxidation refers to the increase in oxidation state of a molecule, often involving the addition of oxygen or the removal of hydrogen. Recognizing how different functional groups react under oxidation conditions is crucial for predicting products. For instance, knowing that alcohols can be oxidized to aldehydes or acids helps in determining the expected outcomes of reactions with PCC and H₂CrO₄.
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Related Practice
Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (xi) HOCl, H2O (xii) HIO4 If no reaction occurs, write 'no reaction.'


(k)

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Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (v) 1. TsCl, Et₃N 2. NaOt-Bu (vi) H₂SO₄ If no reaction occurs, write 'no reaction.'

(k)

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Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (iii) SOCl₂ , NEt₃, and (iv) 1. TsCl, Et₃N 2. NaCN. If no reaction occurs, write 'no reaction.'

(k)

1
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Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (ix) PCC; (x) H₂CrO₄ , H₂O. If no reaction occurs, write 'no reaction.'

(o)

1
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Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (iii) SOCl₂ , NEt₃ (iv) 1. TsCl, Et₃N 2. NaCN; If no reaction occurs, write 'no reaction.'

(o)

1
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Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (vii) HCl; (viii) HBr; If no reaction occurs, write 'no reaction.'

(o)

2
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