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A problem set for organic chemistry chem 231a students. It includes various tasks such as identifying names and structures of molecules, predicting products of reactions, and explaining the reactivity of lithium diisopropyl amide (lda).
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Problem Set # Due Thursday, October 9 at 12:00 pm 40 points total
1e. Choose one of the above molecules and draw its enantiomer and at least two non-enantiomeric diastereomers.
HO
Br
O O 2c
2c
2c
OH
O O
O 2d. Consider the molecule from question 2c3. If two mole equivalents of LDA are used, a second reaction results in the formation of a product with the formula C 6 H 7 O 4 Li. What is the structure of this product? Write a mechanism that accounts for the formation of this product. Why would 2 equivalents be needed for this reaction to occur? Explain. (3 pts)
N Li +
LDA
Br
Cl
1a.
I
1c.
1d.
(2R, 3S, 4R) 1-bromo-4-chloro-3-isopropyl-2,4,5-trimethylhexane
H
(2S, 3S, 4S, 5R, 6R) 2-bromo-3-t-butyl-5-ethyl-4-isopropyl-6-trifluoromethyloctane
1b.
O
HO
3a
Br 3b NH^2
3c H
O
CH (^3)
H 2 O
F OH
O
OH