Ch. 13 - Alcohols and Carbonyl CompoundsSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins

Concept #1: Oxidizing Agents

Example #1: Which compounds can be oxidized?

Example #2: Oxidizing with strong agent

Example #3: Oxidizing with weak agent

Concept #2: Jones Reagent Mechanism

Concept #3: Intro

Practice: What is the product of the reaction?

Practice: What is the product of the reaction?

Practice: What is the product of the reaction?

Additional Problems
Complete the mechanism for the following oxidation of an aldehyde reaction. Draw all the arrows to indicate movement of electrons, write all lone pairs, all formal charges, and all the products for each step. In the dotted box write which mechanistic element is involved in each step.
Show how the starting material can be converted to the product. Show all the reagents you need and indicate the stereochemistry when appropriate. If a racemic mixture is formed, draw both enantiomers and write “racemic” next to the two structures. You do not need to show arrow pushing like in a mechanism question, only the reactions. All carbon atoms in the products should come from the starting material. Use as many molecules of the starting material as you might need to get to the product.
Oxidation of a 3° alcohol with chromic acid results in the production of ________. a. an ester b. a ketone c. an aldehyde d. a carboxylic acid e. none of these
Identify the reactants (1˚, 2˚, 3˚ alcohol, aldehyde, etc.) and then draw the organic product of each reaction. If no reaciton occurs, write 'NR'.  
Fill in the box with the product(s) that are missing from the chemical reaction equation. Draw only the predominant regioisomer product or products (i.e. Markovnikov or non-Markovnikov products) and please remember that you must draw the structures of all the product stereoisomers using wedges and dashes to indicate stereochemistry. When a racemic mixture is formed, you must write "racemic" under both structures EVEN THOUGH YOU DREW BOTH STRUCTURES.
Fill in the box with the product(s) that are missing from the chemical reaction equation. Draw only the predominant regioisomer product or products (i.e. Markovnikov or non-Markovnikov products) and please remember that you must draw the structures of all the product stereoisomers using wedges and dashes to indicate stereochemistry. When a racemic mixture is formed, you must write "racemic" under both structures EVEN THOUGH YOU DREW BOTH STRUCTURES.
Fill in the box with the product(s) that are missing from the chemical reaction equation. Draw only the predominant regioisomer product or products (i.e. Markovnikov or non-Markovnikov products) and please remember that you must draw the structures of all the product stereoisomers using wedges and dashes to indicate stereochemistry. When a racemic mixture is formed, you must write "racemic" under both structures EVEN THOUGH YOU DREW BOTH STRUCTURES.
Predict the organic product(s) of the following reaction. When appropriate, be sure to indicate stereochemistry. If more than one product is formed be sure to indicate the major product. Draw all answers in skeletal form.
Predict the organic product of the following reaction. When appropriate, be sure to indicate stereochemistry. If more than one product is formed be sure to indicate the major product. Draw your answer in skeletal form. You will be graded on the product your draw from the reaction no other information is needed for this question.
Draw the structure of the alcohols, which are the direct precursors of the following carbonyl derivatives. Which reagent would you use to achieve these transformations?
Which of the following compounds can be oxidized using CrO3/pyridine? 1) A only 2) B only 3) C only 4) A and B only 5) B and C only
What is the expected product from this oxidation?
Which compound can be most easily oxidized by K2Cr2O7 + H2SO4?
   
Benzaldehyde (shown below) can be oxidized with Jone’s reagent, but not benzophenone. Why? Please explain it with less than 15 words.
What are the chemical components of Jone’s reagent?
What are the full name and the chemical structure of PCC oxidizing reagent?
For the reaction shown below, draw the structure of the major product(s). Where appropriate write “No Reaction”. Assume all chiral starting materials are optically pure. Show stereochemistry where appropriate. For products that exist as a single enantiomer place an “x” in the box in the lower right corner of the answer space. If the product exists as a racemic mixture place an “x” in the circle.
Complete the following reaction by drawing the structure of the principal major product. Indicate relative stereochemistry where necessary. If there is no reaction, write NR.
Predict the product for the following reaction.   
An unknown compound is not oxidized by chromic acid solution. When dissolved in Lucas reagent (conc. HCl/ZnCl2), the solution immediately becomes cloudy with the separation of a second liquid phase. Which compound is consistent with this data?
Predict the product:
What is the major product of the following rxn:  
Supply the reagents:
Predict the product:
Predict the organic product(s) of the following reaction. When appropriate, be sure to indicate stereochemistry. Be sure to indicate the major product if more than one product is formed. Draw all answers in skeletal form. 
Give the major product for the following reaction
Draw major organic product of the reaction shown below. You do not have to consider stereochemistry You do not have to explicitly draw H atoms. In cases where there is more than one answer, just draw one.
Draw the structural formula for the intermediate species that forms when the following compound is treated with K2Cr2O7. • You do not have to consider stereochemistry.• You do not have to explicitly draw H atoms. 
Draw the major organic product when the following are treated with acidic K2Cr2O7. It no reaction occurs draw the reactant.
The reaction in the figure below indicates the oxidation of cyclohexanol with chromic acid. Write the systematic IUPAC name for the product in the space below. If you cannot see the image, close your browser window and reload the test.
Draw the product formed through the following reaction.
Draw the organic product (if any) expected from the following oxidation reaction:  
Select the appropriate reagents for the following transformation:
Draw the correct organic product for the following oxidation reaction: 
Identify a suitable reagent to carry out the following transformation. a. NaOH b. PCC c. 1. NaCN, 2. H+, H2O d. Na2CrO7, H2O, H2SO4
Provide the major organic product of the reaction shown. 
Draw the products formed through the following reaction.
Draw the correct product for the following reaction. (if there is no reaction, draw the starting material.)  
Which of the following compounds when oxidized (loss of hydrogens) produces a ketone? Select one:  
Give the major product for the following reaction.  
Draw the organic product (if any)expected from the following reaction: (include all hydrogen atoms) 
Albuterol is a prescription medication for treating asthma, bronchitis and symptoms associated with COPD. It functions as a Bradrenergic receptor agonist that relaxes the muscles in the airways. As a chemist, you have been consulted on how to convert albuterol to the product (oxoalbuterall) shown below for pre-clinical trials. Select the appropriate reagent from the drop-down list for this transformation. 
Give the product expected when the following alcohol reacts with pyridinium chlorochromate (PCC) (Assume that PCC is present in excess.)
Give the oxidation product of the following alcohol if a mild oxidizing agent is used. If no reaction occurs, select N.R.  CH3CH2CH2OH  
Draw the correct product for the following reaction. (If there is no reaction, draw the starting material.)
Draw the correct organic product of the following oxidation reaction:
Provide the major organic product of the reaction shown.  
Draw the major organic product of the reaction shown below. 
Give the product expected when the following alcohol reacts with pyridinium chlorochromate (PCC). (Assume that PCC is present in excess.)
Draw the correct product for the following reaction. (If there is no reaction, draw the starting material.)
Draw the major organic product of the reaction shown below. 
Give the product expected when the following alcohol reacts with pyridinium chlorochromate (PCC). (Assume that PCC is present in excess.)
Which reagent would accomplish this conversion?
Which of the following could be oxidized to give a ketone?