Ch. 14 - Synthetic TechniquesWorksheetSee 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
Sections
Synthetic Cheatsheet
Moving Functionality
Alkynide Alkylation
Alkane Halogenation
Retrosynthesis

The idea here is that we will be given a target molecule and the reactant and have to work backwards to fill in the missing pieces. 

 

Let's get started!

Concept #1: Intro

As mentioned in the above video, some of these transformations may be harder than you need to know. Also, know that there are multiple ways to achieve one product but it is important to find the most effective and shortest way possible

 

Time to put those skills to the test :)

Practice: Supply the reagents necessary to accomplish the following transformation.

Practice: Propose a synthesis

Practice: Supply the reagents necessary to accomplish the following transformation.

Additional Problems
Show how you would carry out each of the following reactions. You do   NOT need to draw the mechanisms
Show how you would carry out each of the following reactions. You do   NOT need to draw the mechanisms  
Show how you would carry out each of the following reactions. You do   NOT need to draw the mechanisms
Show how you would carry out each of the following reactions. You do   NOT need to draw the mechanisms
Fill in all structures in the boxes provided for the reaction scheme indicated. Appropriate work ups are assumed when not indicated.
Propose a synthetic way to produce each of the following compounds
Fill in the following synthetic map dealing with alcohols. 
Which of these methods will produce 1-pentanol? 
Compound A has molecular formula C5H10. When A is treated with BH3, followed by H2O2, NaOH, H2O, a mixture of B and B’ is isolated. B and B’ each have molecular formula C5H12O. Separately, B and B’ are optically active. A 50:50 mixture of B and B’ is optically inactive, however. When the mixture of B and B’ is exposed to the Jones reagent (CrO3, H2SO4, H2O), a single compound C (C5H10O) is produced. Finally, when A is treated with O3 followed by H2O2, acetone (shown below) and Compound D (C2H4O2) are produced. Complete the reaction scheme below by drawing structures for the unknown compounds A, B, B’, C and D. Be sure to show the stereochemistry of B and B’ clearly and unambiguously!
Outline a series of synthetic steps which would efficiently accomplish the conversion. You may use any organic compound with two or less carbons, and any inorganic reagent. Give a step-by-step outline and do not give mechanisms.