6 5 OCH 3 1) Excess CH3MgBr 2) pH adjust to 7.0 3) PBr3 4) ? 3 PPM A (C5H10)

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Chapter1: Chemical Foundations
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6
The ester shown below was subjected to the indicated
sequence of chemical reactions to yield compound A (C5H10) with its ¹H-
NMR spectrum shown below
- Identify the missing step #4 and give the structure of A.
- Clearly show how your structure is consistent with the spectral data
Show a reasonable mechanism that accounts for the formation of A in
each of the four steps.
O
CT
OCH 3
4
1) Excess CH3MgBr
2) pH adjust to 7.0
3) PBr3
4) ?
3
PPM
2
A (C5H10)
0
Transcribed Image Text:6 The ester shown below was subjected to the indicated sequence of chemical reactions to yield compound A (C5H10) with its ¹H- NMR spectrum shown below - Identify the missing step #4 and give the structure of A. - Clearly show how your structure is consistent with the spectral data Show a reasonable mechanism that accounts for the formation of A in each of the four steps. O CT OCH 3 4 1) Excess CH3MgBr 2) pH adjust to 7.0 3) PBr3 4) ? 3 PPM 2 A (C5H10) 0
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