Chemistry 331 - Fall 1996

Chapter 7 - Alkyl Halides

Practice Exercises

Reactions

Write out all the possible products that could be formed by monochlorination of methylcyclobutane.

Complete each of the following reactions:

Reaction Mechanisms

Describe the ways you could experimentally distinguish whether a particular substitution reaction followed an SN1 or an SN2 pathway.

Describe the ways you could experimentally distinguish whether a particular elimination reaction followed an E1 or an E2 pathway.

Write potential energy diagrams that distinguish the different pathways.

Write the transition states for the rate-determining step of each pathway.

Substitution and Elimination

Predict and/or control what a given compound is likely to do under certain circumstances

How can you make ... react in an ... mechanism ?

	SN1	SN2	E1	E2
CH3X	No	good nucl.	No	No
1° ( RCH2X )	No	good nucl., weak base	No	strong base, weak nucl.
2° (R2CHX )	No	good nucl., weak base	No	strong base
3° ( R3CX )	good nucl., weak base	No	polar solvent, no base or nucl.	strong base

What's most likely to happen when ... reacts with ... ?

	Good nucl., strong base, e.g., OH-	Good nucl., weak base, e.g., I-	Poor nucl., strong base, e.g., tBuO-	Poor nucl., weak base, e.g., H2O
CH3X	SN2	SN2	SN2	No reaction
1° ( RCH2X )	SN2	SN2	E2	No reaction
2° (R2CHX )	E2	SN2	E2	No reaction
3° ( R3CX )	E2	SN1	E2	SN1