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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.

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.

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter6: Alkanes & Alkenes
Section: Chapter Questions
Problem 21CTQ
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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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