Ch. 12 - Alcohols, Ethers, Epoxides and ThiolsSee 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

Leaving Group Conversions - Sulfonyl Chlorides

See all sections

Now that we’ve covered alkyl halides, sulfonyl chlorides can be used to convert alcohols into another great leaving group: sulfonate esters.

Concept #1: Learning the mechanism of Sulfonyl Chlorides.

This conversion proceeds without the use of SN2, meaning that we expect retention of configuration.

Yes we know, there is an extra methyl in the original molecule in the video. However, we decided to remove it completely from the problem. 

 

This allows for a backside attack to successfully take place in the last step (seen by the blue Nu-). 

Additional Problems
Predict the major organic product(s) of the following reactions. Clearly show the stereochemistry of the products where isomers are possible. Indicate the reaction type (ex. SN2/E2/SN1/E1) on the line next to the product box.
Supply the missing inorganic reactant (reagent) or catalyst for the reaction given below.
Provide an organic reaction in which the given intermediate or transition-state structure is involved and give a chemical equation for your selected organic reaction that includes the following in each of your answers: (i) structural formula(s) for the organic reactant(s) [Be sure to show stereochemistry clearly when necessary.]; (ii) a structural formula for the major organic product [Be sure to show stereochemistry clearly when necessary.]; (iii) the experimental conditions (Give structural formulas for organic compounds. Give a chemical formula for inorganic reactants or catalysts . If heat and/or light is needed, be sure to indicate it appropriately.) As we do for most organic reaction equations, the chemical equations that you give do not need to be balanced. Be sure to show stereochemistry clearly when necessary.
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.
Predict the product of the following reaction, showing stereochemistry if applicable. If there is no reaction, just write “no reaction” in the box.
Provide the major product for the following compound.
What are structures of mesyl chloride and tosyl chloride?
For the reaction or series of reactions below, draw the structure of the product in the box. Be sure to clearly indicate stereochemistry where this is pertinent. Give only one answer.
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 other stereoisomer formed. (enantiomers, diastereomers, etc.).
Predict the products of the following synthesis: 
The transformation of the hydroxyl group into a good leaving group can be accomplished through the use of various reagents. 
Hydroxyl groups can be transformed into tosylate, which is a good leaving group that retains the original stereochemistry. Determine the products in each of the steps of this synthesis reaction. 
Which set of reagents will best accomplish the following transformation?
 Provide the major product for the following reaction. 
Create the full arrow pushing mechanism which shows all intermediates and all products that result from these reactions and label minor and major products if they are not equal in potential energy.
Write the structural formula of the main organic product for the following reaction between an alcohol, tosyl and then a nucleophile. Product structural formula formatting counts: enter C before associated H atoms, Subscript 1.TsCI numbers) (e.g.. CH3CH2CHpCHCHCH3). pyridine CH,CH,0H 2.Cl 
Give the major product of the following reaction.
This question has multiple ports. Work all the part, to get the most points. For the reaction below: Draw the major organic product(s) in the sketch pad below. If the reaction produces a racemic mixture, draw both stereoisomers.
The tosylate of (2R,3S) -3-phenylbutan-2-ol undergoes an E2 elimination on treatment with sodium ethoxide: Draw the structure of the alkene that is produced. Use the wedge/hash bond tools to indicate stereochemistry. You do not have to explicitly draw H atoms. If a group is achiral, do not use wedged or hashed bonds on it.
Predict the product for the following reaction.
What is the major organic product obtained from the following sequence of reactions?a. (R)-2-Methoxypentaneb. (S)-2-Methoxypentanec. (t)-2-Methoxypentaned. trans-2-Butene  
Draw the major organic product of the following reaction. Indicate the stereochemistry, if appropriate. Use a wavy bond to indicate a mixture of configurations.
Predict the major product of the following reaction and then draw a stepwise mechanism for the reaction:
Draw a structure for the expected product of the reaction below.  
Write the structural formula of the main organic product for the following reaction between an alcohol chloride, and then a nucleophile. Product structural formula (formatting counts: enter C before associated H atomsi subscript numbers)
Write the structural formula of the main organic product for the following reaction between an alcohol, tosyl chloride, and then a nucleophile.