Part 1: Synthesis of Ligand. In this experiment you prepare the chiral ligand 4 by first converting the salt 2 to its free amine 2' then condensing it with aldehyde 3a to give bis-imine 4. t-Bu t-Bu „NH3 O2C HO NH2 OH i) K2CO3 ethanol, reflux "NH3 O2C "., “NH2 OH OH t-Bu t-Bu 2 2' t-Bu t-Bu За 1. NMR analysis of compound 4 is not performed. By comparing the structures of free amine 2' and aldehyde 3a with the bis-imine 4 indicate which two signals in the 'H-NMR (of 4) would be most useful to confirm its formation? Ensure you explain your answer and use appropriately labelled diagrams to illustrate. (Hint. Which chemical environments change the most when forming 4 from 2' and 3a)

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Part 1: Synthesis of Ligand. In this experiment you prepare the chiral ligand 4 by first converting the
salt 2 to its free amine 2' then condensing it with aldehyde 3a to give bis-imine 4.
t-Bu
t-Bu
„NH3 O2C
HO
NH2
OH
i) K2CO3
ethanol, reflux
"NH3 O2C
".,
“NH2
OH
OH
t-Bu
t-Bu
2
2'
t-Bu
t-Bu
За
1. NMR analysis of compound 4 is not performed. By comparing the structures of free amine 2' and
aldehyde 3a with the bis-imine 4 indicate which two signals in the 'H-NMR (of 4) would be most
useful to confirm its formation? Ensure you explain your answer and use appropriately labelled
diagrams to illustrate. (Hint. Which chemical environments change the most when forming 4 from
2' and 3a)
Transcribed Image Text:Part 1: Synthesis of Ligand. In this experiment you prepare the chiral ligand 4 by first converting the salt 2 to its free amine 2' then condensing it with aldehyde 3a to give bis-imine 4. t-Bu t-Bu „NH3 O2C HO NH2 OH i) K2CO3 ethanol, reflux "NH3 O2C "., “NH2 OH OH t-Bu t-Bu 2 2' t-Bu t-Bu За 1. NMR analysis of compound 4 is not performed. By comparing the structures of free amine 2' and aldehyde 3a with the bis-imine 4 indicate which two signals in the 'H-NMR (of 4) would be most useful to confirm its formation? Ensure you explain your answer and use appropriately labelled diagrams to illustrate. (Hint. Which chemical environments change the most when forming 4 from 2' and 3a)
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