A chemist attempted the following synthesis but obtained only a very low yield of the desired product. What went wrong? 1) DCCD HO,C "CO,H HO,C `N' 2) Н,N \CO,H `N' HN, mCO,H t-BOC t-BOC C,H5 C,H, DCCD can activate both carboxylic acid groups, so that both will react with the amino acid added in the second step. O The t-BOC group is not stable to the reaction conditions. O The second amino acid has to be added before the DCCD is added. O DCCD is the incorrect reagent for effecting peptide bond formation.

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A chemist attempted the following synthesis but obtained only a very low yield of the desired
product. What went wrong?
1) DCCD
HO,C
"CO,H
HO,C
`N'
2) Н,N
CO,H
`N'
HN,
mCO,H
t-BOC
t-BOC
C,H5
C,H,
DCCD can activate both carboxylic acid groups, so that both will react with the amino acid added in the
second step.
O The t-BOC group is not stable to the reaction conditions.
O The second amino acid has to be added before the DCCD is added.
O DCCD is the incorrect reagent for effecting peptide bond formation.
Transcribed Image Text:A chemist attempted the following synthesis but obtained only a very low yield of the desired product. What went wrong? 1) DCCD HO,C "CO,H HO,C `N' 2) Н,N CO,H `N' HN, mCO,H t-BOC t-BOC C,H5 C,H, DCCD can activate both carboxylic acid groups, so that both will react with the amino acid added in the second step. O The t-BOC group is not stable to the reaction conditions. O The second amino acid has to be added before the DCCD is added. O DCCD is the incorrect reagent for effecting peptide bond formation.
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