This site requires Javascript to be turned on. Please enable Javascript and reload the page.

Organic Chemistry Main Menu Lecture 1: Introduction to Molecular Orbitals Lecture 10: Intermolecular Forces and Intro to Reactivity Lecture 11: Alkenes as Nucleophiles I Lectures 12 and 13: Alkenes II & III Lecture 14: Benzenes as Nucleophiles I Lecture 15 objectives and skills Lecture 2: Molecular Orbitals in Organic Structures Lecture 3: Molecular Orbitals and Resonance Lecture 4: Molecular Orbitals and Aromaticity Lecture 5: Nomenclature and IR Spectroscopy Lecture 6: Stereochemistry I Lecture 7: Stereochemistry II Lecture 8: Newman and Fisher Projections Lecture 9: Conformations and Cyclohexane Rings

SOLUTION 17.2b

35992

Both S_N1 and S_N2 reactions are possible. Since good nucleophile (OH^-) + secondary alkyl halide, S_N2 is more likely to occur than S_N1. Minor amounts of racemic mixture results from S_N1 pathway (15% R + 15% S) and major amounts of inversion from S_N2 pathway (70% S). Overall: 85% S and 15% R.

This page is referenced by:

Lecture 17: Ionic Substitution (SN1/SN2) I 18 image_header 2020-04-15T16:30:21-07:00
Objectives and Skills

KEY INFORMATION SUMMARY

PROBLEMS

Problem 17.1: Mechanisms
1. Add the curved arrows to complete each transformation below (extra intermediates may need to be drawn). SOLUTION
1. List the following carbocations in decreasing order of their stability. SOLUTION
If you made some mistakes or want to practice more, review the concepts that gave you trouble and work on this extra problem. If you are good, move to the problem below ;)

Problem 17.2: Reaction Coordiate Diagrams
1. Draw a mechanism and reaction coordinate diagram to describe the reaction below. SOLUTION
2. Explain why the major product is favoured. SOLUTION
If you made some mistakes or want to practice more, review the concepts that gave you trouble and work on this extra problem. If you are good, move to the problem below ;)

Problem 17.3: Reactivity
1. Fill in the missing pieces to complete the transformations below. SOLUTION
1. Convert 1-phenylpropane to each of the structures below. SOLUTION
1. Rationalize the following: methyl bromide reacts 10⁵ times faster via S_N2 reaction than neopentylbromide. SOLUTION
If you made some mistakes or want to practice more, review the concepts that gave you trouble and work on this extra problem. If you are good, move to the next lecture ;)