Ch. 13 - Alcohols and Carbonyl CompoundsWorksheetSee 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: Intro to Predict the Product

Practice: Predict the product of the reaction

Practice: Predict the product of the reaction

Practice: Predict the product of the reaction

Practice: Predict the product of the reaction

Concept #2: Intro to Retrosynthesis

Practice: Propose a synthesis to accomplish the following transformation

Practice: Propose a synthesis to accomplish the following transformation

Practice: Predict the product of the reaction

Additional Problems
Predict the missing structures of products or reagents that you may use to accomplish the following transformations. Show the source of incorporation of deuterium and the stereochemistry when appropriate (No mechanism is required).
Provide the reagents necessary for the following conversion. a) 1. CH3CH2MgBr/ether, 2. H3O+, Δ b) 1. NaBH4/CH3OH, 2. CH3CH2MgBr c) 1. H3O+ , CH3CH2MgBr/ether d) CH3CH2MgBr/ether
Propose a sequence of synthetic steps that would efficiently accomplish the conversion shown below. Show all starting materials and necessary reagents, but do not give mechanisms.
Provide a synthetic pathway:
This is a synthesis question. You need to show how the starting material can be converted into the product(s) shown. You may use any reactions you have learned. Show all the reagents you need. Show each molecule synthesized along the way and be sure to pay attention to the regiochemistry and stereochemistry preferences for each reaction. If you make a racemic mixture, you can either draw both enantiomers or simply draw one structure and label all chiral centers with an asterisk (*). Either way, you must write racemic if appropriate.All of the carbon atoms of the products must come from the starting materials.
Predict the product of the following reaction sequence:
Provide a synthetic pathway:
Synthesize alcohol (L) from organic starting materials of 6 carbons or less:
Provide the reagents or starting materials to perform the indicated transformations. More than one reaction may be required. Be sure to number your steps if it is important for the synthetic transformation to take place.
Hydrocarbon (A), C9H16, is chiral, possess a ring of five carbon atoms, contains four methyl groups, and absorbs one equivalent of H2 upon treatment with H2 over nickel catalyst to yield a racemic hydrocarbon, C9H18. When hydrocarbon (A) is treated with peracetic acid (CH3COOOH) and then with CH3MgBr, the major product (after exposure to dilute acid) is a teriary alcohol (B). (B) is not chiral. What is the structure of (A) and (B)?
Provide a synthesis of the following alcohol. All of the carbons in the molecule below must come from cyclopentane. You may use any other reagents that you find necessary.
Provide the reagents to accomplish the following transformations. More than one step might be required for each transformation.
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, if stereoisomers are produced in the reaction be sure to indicate the relationship between them. Draw all answers in skeletal form. 
Provide the reagent or starting material to perform the indicated transformation. More than one reaction may be required. You should number your steps if it is important for the synthetic transformation to take place.
Provide a synthesis of the following compound; starting from the indicated materials for the source of carbon atoms in the target. You may use any other reagents that you find necessary.
Predict the organic product(s) for the following reaction. Be sure to indicate stereochemistry when appropriate. If stereoisomers are produced draw one and state the relationship between the otherstereoisomer formed. (enantiomers, diastereomers, etc.).
Draw the organic product of the below reaction. Do not draw inorganic by-products or counterions. Ignore stereochemistry in the product.
In each reaction box, place the best reagent and conditions from the list below.