A. TLC question. Diol A reacted with 1 equivalent of the Chal (nucleophilic substitution) with a
formation of the mixture of B and C. On the right you see the TLC of the reaction mixture when
all 3 compounds are present.
HO
A
KOH, CH3I
OH
KOH, CH3I
HO
B
R_f = 0.58
R_f = 0.33
R_f = 0.15
C
Based on polarity of A, B and C, match each molecule with its spot on the TLC plate (fill in 3
boxes with letters, one box-one letter of the molecule).
B. Distillation question. Alcohol D oxidized to aldehyde E and then to carboxylic acid F according
to the following scheme. Based on the structures of all 3 molecules, match the boiling points with
a structure of the molecules (fill in 3 boxes with letters, one box-one letter of the molecule).
Higher
OH
CrO3
CrO3
OH
hyhu
D
E
b.p. = 131 °C
b.p. = 92 °C
b.p. = 176 °C
F
C. Extraction question. Reaction mixture (with all 3 molecules)
from part B was extracted with CH2Cl2-water system (see
separatory funnel on the right). Predict the content of
Organic Layer:
Aqueous layer:
H2O + ?
CH2Cl2 + ?