Chapter 6
*****
Groups 7, 15, 17, and 19 prepare to present part I below.
Groups 8, 14, 16, and 20 prepare to present part II below.
*****
Of course, it behooves the entire class to work on the learning group
problems.
*****
I. Consider the solvolysis reaction of
(1S,2R)-1-bromo-1,2-dimethylcyclohexane in 80% H2O/20% CH3CH2OH at room
temperature.
a) Write the structure of all chemically reasonable products from this
reaction and predict which would be the major one.
b) Write a detailed mechanism for formation of the major product.
b) Write the structure of all transition states involved in formation of
the major product.
*****
OR (according to the group assignments above)
*****
II. Consider the following sequence of reactions.
i) 1-bromo-8-fluorooctane + sodium acetylide (the sodium salt of
ethyne)
-------> Compound F (C10H17F)
ii) Compound F + NaNH2 ------> Compound G (C10H16FNa)
iii) Compound G + I-(CH2)7-Cl -----> Compound H (C17H30ClF)
iv) Compound H + NaCN -------> Compound I (C18H30NF)
a) Elucidate the structure of compounds F, G, H, and I above.
b) Write the mechanism for each of the reactions above.
c) Write the structure of the transition state for each reaction.
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055
Associate Professor Email fryhle@u.washington.edu
Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html
Pacific Lutheran University
Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^
^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^
^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^