Reagents Available g. CO, HCI, CUCI/AICI3 h. CH3CH2CH2COCI, AICI3 a. CH2=CHCH,CI, AICI3 b. CH2Br2, OH c. CH3CH,COCI, AICI3 d. H2, Pt e. NBS, CCI4 f. K* tBuO¯ i. BRCH2CH,Br, OH j. CH3CH2CI, AICI3 k. RCO3H CH=CHCH3 I. H3O* Using conditions from the table, show how you would synthesize this compound from catechol (1,2-benzenediol). Select reagents from the table in the order that you wish to use them, i.e. aced; do not include punctuation or spaces. If more than one route exists, choose the shorter one; in no case will a synthesis require more than 5 steps.

Chemistry
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Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Reagents Available
a. CH2=CHCH,CI, AICI3
b. CH2Br2, OH
c. CH3CH,COCI, AICI3
d. H2, Pt
e. NBS, CCI4
f. K* tBuO
g. CO, HCI, CUCI/AICI3
h. CH3CH2CH2COCI, AICI3
i. BrCH2CH2Br, OH-
j. CH3CH2CI, AICI3
k. RCO3H
I. H3O*
CH=CHCH3
Using conditions from the table, show how you would synthesize this compound from catechol (1,2-benzenediol).
Select reagents from the table in the order that you wish to use them, i.e. aced; do not include punctuation or spaces.
If more than one route exists, choose the shorter one; in no case will a synthesis require more than 5 steps.
Transcribed Image Text:Reagents Available a. CH2=CHCH,CI, AICI3 b. CH2Br2, OH c. CH3CH,COCI, AICI3 d. H2, Pt e. NBS, CCI4 f. K* tBuO g. CO, HCI, CUCI/AICI3 h. CH3CH2CH2COCI, AICI3 i. BrCH2CH2Br, OH- j. CH3CH2CI, AICI3 k. RCO3H I. H3O* CH=CHCH3 Using conditions from the table, show how you would synthesize this compound from catechol (1,2-benzenediol). Select reagents from the table in the order that you wish to use them, i.e. aced; do not include punctuation or spaces. If more than one route exists, choose the shorter one; in no case will a synthesis require more than 5 steps.
ethers can be prepared by nucleophilic aromatic substitution between a phenolate anion and a deactivated aryl halide. The reaction involves the
on of a resonance-stabilized, negatively charged intermediate called a Meisenheimer complex; elimination of the halide ion completes the reaction.
NO2
O K*
.CO2CH3
CI.
CO2CH3
CI
F3C
`NO2
ČF3
e structure of the Meisenheimer complex formed in this reaction.
You do not have to consider stereochemistry.
Do not include counter-ions, e.g., Na*, I', in your answer.
In cases where there is more than one answer, just draw one.
Transcribed Image Text:ethers can be prepared by nucleophilic aromatic substitution between a phenolate anion and a deactivated aryl halide. The reaction involves the on of a resonance-stabilized, negatively charged intermediate called a Meisenheimer complex; elimination of the halide ion completes the reaction. NO2 O K* .CO2CH3 CI. CO2CH3 CI F3C `NO2 ČF3 e structure of the Meisenheimer complex formed in this reaction. You do not have to consider stereochemistry. Do not include counter-ions, e.g., Na*, I', in your answer. In cases where there is more than one answer, just draw one.
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