Textbook Question
Tertiary (3°)alcohols are not oxidized by chromic acid. Why?
1
views
Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
Not the one you use?Change textbookSelect a different textbook
Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
All textbooks
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 53e
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 53eChapter 12, Problem 53e
The intermediates for the oxidation of isopropanol to acetone are shown. Calculate oxidation numbers for the indicated atoms, then use them to determine in which step oxidation occurs.
(e) 
Verified step by step guidance1
Identify the structure of isopropanol (C3H8O) and acetone (C3H6O). Note that isopropanol is a secondary alcohol, and acetone is a ketone.
Determine the oxidation number of the carbon atom in isopropanol that is bonded to the hydroxyl group (OH). In organic compounds, carbon typically has an oxidation number of -4, but this can vary based on its bonding.
Calculate the oxidation number of the same carbon atom in acetone. Remember that in a ketone, the carbonyl carbon is bonded to an oxygen atom, which is more electronegative.
Compare the oxidation numbers of the carbon atom in isopropanol and acetone. An increase in the oxidation number indicates oxidation.
Identify the step in the reaction mechanism where the oxidation number of the carbon atom increases, signifying the oxidation step in the conversion of isopropanol to acetone.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
3mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Oxidation Numbers
Oxidation numbers are a way of keeping track of electrons in atoms as they undergo chemical reactions. They are assigned to atoms based on a set of rules, such as the oxidation number of a free element being zero and the sum of oxidation numbers in a neutral compound being zero. Calculating oxidation numbers helps identify which atoms are oxidized or reduced in a reaction.
Recommended video:
Guided course
03:40
Strong oxidizing agents
Oxidation and Reduction
Oxidation is the process where an atom loses electrons, resulting in an increase in its oxidation number, while reduction is the gain of electrons, leading to a decrease in oxidation number. In organic chemistry, oxidation often involves the addition of oxygen or the removal of hydrogen. Identifying oxidation and reduction steps is crucial for understanding reaction mechanisms.
Recommended video:
Guided course
00:54Distinguishing between Oxidation and Reduction
Reaction Intermediates
Reaction intermediates are transient species that appear in the steps between reactants and products in a chemical reaction. They are often unstable and cannot be isolated under normal conditions. Understanding intermediates is essential for mapping out the reaction pathway and determining where oxidation or reduction occurs in multi-step processes.
Recommended video:
Guided course
04:31Stability of Conjugated Intermediates
Related Practice
Textbook Question
Predict the product of the oxidation reactions shown.
(a)
Textbook Question
If there is no water present, the hydrate of an aldehyde cannot form. Could an aldehyde itself (not the hydrate) be oxidized to a carboxylic acid? Why?
6
views
Textbook Question
Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.
(d)
1
views
Textbook Question
Predict the product of the oxidation reactions shown.
(b)
5
views
Textbook Question
Though ketones, like aldehydes, are in equilibrium with a hydrated form, they cannot be further oxidized. Why?
1
views