Ch. 8 - Elimination ReactionsWorksheetSee 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

Alkyl halides aren't the only type of leaving groups out there. Let's explore some of the other types that exist. 

Concept #1: The 3 important leaving groups to know. 

1. Alkyl Halides

We’ve been dealing with these the whole lesson, formula –RX. You should be cool with these

 

2. Sulfonate Esters

These are molecules with the general structure –OSO2R or –SO3R. These are the ultimate leaving groups of organic chemistry. They might look a little weird, but in the end of the day, remember they just leave. NBD. 

3. Water

Also an awesome leaving group, formed after alcohol is protonated with a strong acid.

Additional Problems
Rank the following in decreasing order of leaving group ability. a) I > III > IV > II b) I > III > II > IV c) III > II > I > IV d) II > I > III > IV
Which SN1 reaction of each pair would you expect to take place more rapidly? Explain your answer.  
Which of the following undergoes a substitution reaction with sodium cyanide in DMSO at the fastest rate? a) CH3CH2F b) CH3CH2Cl c) CH3CH2Br d) CH3CH2I
Many SN2 reactions of alkyl chlorides and alkyl bromides are catalyzed by the addition of sodium or potassium iodide. For example, the hydrolysis of methyl bromide takes place much faster in the presence of sodium iodide. Explain.  
What is the leaving group in the following reaction? CH3CH2OH  +  HCl  →  CH3CH2Cl  +  H2O a) OH - b) H2O c) CH3CH2- d) Cl -
Which of the following undergoes SN1 solvolysis in ethanol/water at the fastest rate? 
Listed below are several hypothetical nucleophilic substitution reactions. None is synthetically useful because the product indicated is not formed at an appreciable rate. In each case provide an explanation for the failure of the reaction to take place as indicated. 
Listed below are several hypothetical nucleophilic substitution reactions. None is synthetically useful because the product indicated is not formed at an appreciable rate. In each case provide an explanation for the failure of the reaction to take place as indicated. 
Listed below are several hypothetical nucleophilic substitution reactions. None is synthetically useful because the product indicated is not formed at an appreciable rate. In each case provide an explanation for the failure of the reaction to take place as indicated. 
Listed below are several hypothetical nucleophilic substitution reactions. None is synthetically useful because the product indicated is not formed at an appreciable rate. In each case provide an explanation for the failure of the reaction to take place as indicated. 
Listed below are several hypothetical nucleophilic substitution reactions. None is synthetically useful because the product indicated is not formed at an appreciable rate. In each case provide an explanation for the failure of the reaction to take place as indicated. 
For the following pairs of reactions, mark an “X” in the box on the right indicating which will go faster. The compound on top of the arrow is the solvent.
Can methyl fluorides (e.g., CH3F) undergo substitution? Explain in one sentence.