Organic Chemistry Practice Problems can be found after each topic covered in Chemistry Steps. The list of topics can be found here, and below are some examples of what you will find.
Refer to this post if you are seeking synthesis problems tailored for Organic Chemistry 1 classes.
Organic Chemistry 1 Synthesis Problems
Nucleophilic Substitution and Elimination Reactions
Practice Problems
Predict the mechanism as SN1, SN2, E1 or E2 and draw the major organic product formed in each reaction. Consider any regioselectivity and stereoselectivity where applicable:
Reactions of Alkenes Practice Problems
This is a comprehensive problem that covers the following topics and will serve as a review of all of them:
Substitution and elimination reactions. Particularly, substitution and elimination reactions of alcohols, the regio– and stereochemistry of E2 reactions, and E2 reaction of cyclohexanes.
Mesylation and tosylation in Substitution and elimination reactions.
Hydrohalogenation of alkenes according to Markovnikov’s rule.
Radical hydrohalogenation of alkenes.
Hydroboration-Oxidation of Alkenes.
Halogenation of alkenes through halohydrin formation.
Syn and anti dihydroxylation of alkenes.
Elimination reactions: Zaitsev and Hoffman products.
Ozonolysis of Alkenes.
Attempt to solve the entire problem before accessing the answers!
The answers will give you the structure of the final product(s) only. Use this as a hint to determine the compounds formed after the first and second reactions.
Complete the following synthesis by adding the missing reagent(s) for each step and the structures for compound A and B:
Complete the following synthesis by adding the missing reagent(s) for each step and the structures for compound A and B:
Complete the following synthesis by adding the missing reagent(s) for each step and the structures for compound A and B:
Reactions of Alkynes Practice Problems
On the following synthetic scheme, identify the reagents, in the correct order, that you would use to achieve the following synthetic transformations. Determine the structure of compounds A and B and the major organic products resulting from the alkyne.
Organic Chemistry 2 Practice Problems
Alcohols Practice Problems
Predict the major organic product(s) for the following Grignard reactions of a ketone, aldehyde, ester, carbon dioxide and an epoxide:
The Diels-Alder Reaction Practice Problems
For each Diels–Alder reaction, predict the major product(s) with correct stereochemistry when each cyclic diene is reacted with a dienophile:
Aromatic Substitution Practice Problems
Show how each compound can be synthesized from benzene and any other organic or inorganic reagents.
The order of reactions is very important! So, before every step, consider the ortho– , para– , or meta directing effect of the current group on the aromatic ring.
Devise a synthesis of each of the following compounds using an arene diazonium salt. They all require more than one step and you may select the desired regioisomer (for example the para product from an ortho, para mixture) when needed.
Aldehydes and Ketones Practice Problems
Predict the major product(s) obtained when each of the following compounds undergoes hydrolysis in the presence of an acid:
Carboxylic Acids and Their Derivatives Practice Problems
Predict the major organic product(s) for each of the following reactions. They all involve carboxylic acid derivatives such as esters, acid chlorides, nitriles, anhydrides, and amides. You may also need to go over the reactions covered in earlier chapters, particularly, the Grignard and Gilman reagents, oxidizing and reducing agents and electrophilic aromatic substitutions.
A link to each topic encountered in a given problem will be provided in the answer tab.
Alpha Carbon Chemistry – Enols and Enolates Practice Problems
This is a comprehensive practice problem on the alpha carbon chemistry. The topics covered range from the simple halogenation reactions of enols to multistep synthetic transformation.
To correctly answer these questions, you need to review the main principles of enolate chemistry – direct enolate alkylation, aldol condensation, crossed aldol condensation, alkylation using acetoacetic ester synthesis, malonic ester synthesis, the Stork enamine synthesis, Claisen condensation, Michael addition, and Robinson annulation.
Practice
CS Prime membership will also grant you access to multiple-choice quizzes!
If you are towards the end of your Organic 2 semester having covered most of the topics and ready for some more challenging synthesis problems – you are in the right place! In these practice problems, we will go over multistep organic synthesis.
Check also our new synthesis puzzles!
Go ahead and give it a try!
