Question

c) Draw the major products E, F and G that would be formed in the following reactions. (20 Marks) i) $\xrightarrow{\text{mCPBA} \\ \text{CHCl}_3}$ E ii) $\xrightarrow{\text{mCPBA} \\ \text{CHCl}_3}$ F iii) $\xrightarrow{\text{Jones Reagent} \\ \text{Acetone}}$ G d) Propose a synthetic approach to prepare the following compound using the given starting material. Note that the approach requires a protecting group. (20 Marks) HO O $\longrightarrow$ HO OH e) Draw the structures of the products H and I that would be obtained in the following reactions. (20 Marks) (I) 1a. DIBAL-H (2eq) toluene -78 °C $\xrightarrow{\text{acetal hydrolysis}}$ H CO$_2$Et b. MeOH workup (II) a. DMSO, (COCl)$_2$ $\xrightarrow{\text{CH}_2\text{Cl}_2, -50 ^\circ\text{C}}$ I OH b. Et$_3$N -50 °C to 0 °C c. H$_2$O workup

          c) Draw the major products E, F and G that would be formed in the following
reactions. (20 Marks)
i)
$\xrightarrow{\text{mCPBA} \\ \text{CHCl}_3}$ E
ii)
$\xrightarrow{\text{mCPBA} \\ \text{CHCl}_3}$ F
iii)
$\xrightarrow{\text{Jones Reagent} \\ \text{Acetone}}$ G
d) Propose a synthetic approach to prepare the following compound using the given
starting material. Note that the approach requires a protecting group. (20 Marks)
HO
O
$\longrightarrow$
HO
OH
e) Draw the structures of the products H and I that would be obtained in the following
reactions. (20 Marks)
(I)
1a. DIBAL-H (2eq)
toluene
-78 °C
$\xrightarrow{\text{acetal hydrolysis}}$ H
CO$_2$Et
b. MeOH
workup
(II)
a. DMSO, (COCl)$_2$
$\xrightarrow{\text{CH}_2\text{Cl}_2, -50 ^\circ\text{C}}$ I
OH
b. Et$_3$N
-50 °C to 0 °C
c. H$_2$O workup

c draw the major products e f and g that would be formed in the following reactions 20 marks i xrightarrowtextmcpba textchcl3 e ii xrightarrowtextmcpba textchcl3 f iii xrightarrowtextjones 29546

Added by Timothy S.

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