1. Retro-aldol is an aldol addition reaction in the reverse direction. a. First let's practice recognizing the molecular unit that is the starting material for a retro aldol reaction. Notice that this is the same molecular unit that is formed by aldol addition. Circle the beta hydroxy carbonyl unit in each of the molecules. R1 b. Draw a squiggly line to indicate which bond is cleaved by a retro aldol (see example). HIC i CHO HO. CH3 OH H3C -CH3 H3C OH HO CH3 H3C OH OH OH OH R2 c. Repeat the above for the following molecule and then draw arrow-pushing mechanism for a non-enzymatic retro-aldol reaction. H ད་ག་པའི་ཞུ་ H₂O/HO OH d. Draw arrow-pushing mechanism for an enzymatic retro-aldol reaction of the following hexose. Use B: and/or HA as needed. OH OH OH OH OH e. Check your answer for part d. Use the products you got in part d as reactants for an aldol addition reaction. Write an arrow pushing mechanism for enzymatic reaction
1. Retro-aldol is an aldol addition reaction in the reverse direction. a. First let's practice recognizing the molecular unit that is the starting material for a retro aldol reaction. Notice that this is the same molecular unit that is formed by aldol addition. Circle the beta hydroxy carbonyl unit in each of the molecules. R1 b. Draw a squiggly line to indicate which bond is cleaved by a retro aldol (see example). HIC i CHO HO. CH3 OH H3C -CH3 H3C OH HO CH3 H3C OH OH OH OH R2 c. Repeat the above for the following molecule and then draw arrow-pushing mechanism for a non-enzymatic retro-aldol reaction. H ད་ག་པའི་ཞུ་ H₂O/HO OH d. Draw arrow-pushing mechanism for an enzymatic retro-aldol reaction of the following hexose. Use B: and/or HA as needed. OH OH OH OH OH e. Check your answer for part d. Use the products you got in part d as reactants for an aldol addition reaction. Write an arrow pushing mechanism for enzymatic reaction
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter26: Aldol And Claisen Reactions
Section: Chapter Questions
Problem 27CTQ
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Transcribed Image Text:1. Retro-aldol is an aldol addition reaction in the reverse direction.
a. First let's practice recognizing the molecular unit that is the starting material
for a retro aldol reaction. Notice that this is the same molecular unit that is
formed by aldol addition. Circle the beta hydroxy carbonyl unit in each of
the molecules.
R1
b. Draw a squiggly line to indicate which bond is cleaved by a retro aldol (see example).
HIC i CHO
HO.
CH3
OH
H3C
-CH3
H3C
OH
HO
CH3
H3C OH
OH
OH
OH
R2
c. Repeat the above for the following molecule and then draw arrow-pushing mechanism for a
non-enzymatic retro-aldol reaction.
H
ད་ག་པའི་ཞུ་
H₂O/HO
OH
Transcribed Image Text:d. Draw arrow-pushing mechanism for an enzymatic retro-aldol reaction of the following hexose.
Use B: and/or HA as needed.
OH OH
OH
OH OH
e. Check your answer for part d. Use the products you got in part d as reactants for an aldol
addition reaction. Write an arrow pushing mechanism for enzymatic reaction
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