i) Hac ++ McLafferty rearrangement enol molecular ion at m/z = 58 m/z = 140 100 105 Rectangular Snip 77 1-phenylpentan-1-one 50 120 162 20 40 60 80 100 120 140 160 180 200 mlz b.If a mass spectrum of the ester ethyl pentanoate (CH3CH2CH2CH2CO2CH2CH3) is recorded, what is the mass of the radical cation formed by the McLafferty rearrangement? c. Which of the following compounds can undergo a McLafferty rearrangement? Relative abundance

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In addition to α cleavage, some aldehydes and ketones undergo the McLafferty rearrangement. In the McLafferty rearrangement, a hydrogen on a carbon three atoms from the C=O is transferred to the carbonyl oxygen and a carbon–carbon bond is broken. This process forms an alkene and the radical cation derived from an enol, which appears as a fragment in the mass spectrum.
a.Draw the products formed from the McLafferty rearrangement of 1phenylpentan-1-one, and identify the fragment that results in the given mass spectrum.

i)
Hac
++
McLafferty
rearrangement
enol
molecular ion at
m/z = 58
m/z = 140
Transcribed Image Text:i) Hac ++ McLafferty rearrangement enol molecular ion at m/z = 58 m/z = 140
100
105
Rectangular Snip
77
1-phenylpentan-1-one
50
120
162
20
40
60
80
100 120 140 160 180 200
mlz
b.If a mass spectrum of the ester ethyl pentanoate
(CH3CH2CH2CH2CO2CH2CH3) is recorded, what is the mass of the
radical cation formed by the McLafferty rearrangement?
c. Which of the following compounds can undergo a McLafferty
rearrangement?
Relative abundance
Transcribed Image Text:100 105 Rectangular Snip 77 1-phenylpentan-1-one 50 120 162 20 40 60 80 100 120 140 160 180 200 mlz b.If a mass spectrum of the ester ethyl pentanoate (CH3CH2CH2CH2CO2CH2CH3) is recorded, what is the mass of the radical cation formed by the McLafferty rearrangement? c. Which of the following compounds can undergo a McLafferty rearrangement? Relative abundance
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