A recent article reported that benzylic bromination can be achieved photochemically usingbromotrichloromethane as the brominating agent (you used NBS in lab) as shown below. Draw themechanism of this reaction, labeling all sets as either "Initiation" or "Propagation". Also, show onefeasible termination step. Helpful BDE's are given. How many unique hydrogens (NMR) are present inthe product?BrOrg. Biomol. Chem. 2019, 17, 1384BrCCl3hvМеоOMeМеоOMeOMeОMeBDE of C-Br bond ~230 kJ/molBDE of C-H in HCClg~ 401 kJ/mol

Question
Asked Oct 30, 2019

Could you help me complete this practice problem, I would like to check my work. Thank you for your time!

 

 

A recent article reported that benzylic bromination can be achieved photochemically using
bromotrichloromethane as the brominating agent (you used NBS in lab) as shown below. Draw the
mechanism of this reaction, labeling all sets as either "Initiation" or "Propagation". Also, show one
feasible termination step. Helpful BDE's are given. How many unique hydrogens (NMR) are present in
the product?
Br
Org. Biomol. Chem. 2019, 17, 1384
BrCCl3
hv
Мео
OMe
Мео
OMe
OMe
ОMe
BDE of C-Br bond ~230 kJ/mol
BDE of C-H in HCClg~ 401 kJ/mol
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A recent article reported that benzylic bromination can be achieved photochemically using bromotrichloromethane as the brominating agent (you used NBS in lab) as shown below. Draw the mechanism of this reaction, labeling all sets as either "Initiation" or "Propagation". Also, show one feasible termination step. Helpful BDE's are given. How many unique hydrogens (NMR) are present in the product? Br Org. Biomol. Chem. 2019, 17, 1384 BrCCl3 hv Мео OMe Мео OMe OMe ОMe BDE of C-Br bond ~230 kJ/mol BDE of C-H in HCClg~ 401 kJ/mol

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check_circleExpert Solution
Step 1

Initiation:

hv
Cсl
Br
Br-CCl
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hv Cсl Br Br-CCl

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Step 2

Propagation:

Н
Н
н-с-н
Н-с.
Br
HBr
CH2
CH2Br
ссь
Br-CCI3
+
+
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Н Н н-с-н Н-с. Br HBr CH2 CH2Br ссь Br-CCI3 + +

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Step 3

Terminatio...

CH2
CH2
На На
с.
CI
CI
CI-С -с-CI
CI
Сch,
сь
CI
+
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CH2 CH2 На На с. CI CI CI-С -с-CI CI Сch, сь CI +

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