Ch. 12 - Alcohols, Ethers, Epoxides and ThiolsWorksheetSee 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

Solution: Draw the product(s) of the following reactions.

Problem

Draw the product(s) of the following reactions.

Solution

We’re being asked to draw the products for the given reactions.


Recall that leaving group conversions of alcohols can be achieved using these reagents:

1) HX: alcohols are converted into alkyl halides. The mechanism for this depends on the type of alcohol involved:

1˚ Alcohols: follow an SN2 mechanism

2˚ and 3˚ Alcohols: follow an SN1 mechanism


2) SOCl2 or PBr3: alcohols are converted into alkyl halides. Both reagents follow an SN2 mechanism, with inversion of configuration.


3) Sulfonyl Chloride: alcohols are converted into sulfonyl esters. This proceeds without the use of SN2 mechanism, which means we expect retention of configuration.


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