Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
Section16.SE: Something Extra
Problem 30MP: The carbocation electrophile in a Friede1-Crafts reaction can be generated by an alternate means...
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![1. What product is expected to form in an Sn2reaction of OH¯with (R)-2-bromobutane? Show
the stereochemistry of the reactant and the product.
2. What product is expected to form from the Sy2reaction of 1-bromopentane with
а. КОН?
B. NaI?
3. What product would you expect to obtain from a nucleophilic substitution reaction of (S)-2-
bromohexane with CH3 CO7? Assume that inversion configuration occurs, and show the
stereochemistry of both reactant and product?
4. Predict whether each of the following substitution reactions is likely
be SN 1or SN2.
OAc
CH3CO2 Na+
CH3CO2H, H2O
a.
„CH2Br
.CH2OAC
CH3CO2- Na+
DMF
b.
HCI
CI
HO
CH3OH
с.
CH3
CH3
Na+ SCH3
H2C=CCH2SCH3
H2C=CCH2BR
d.
CH3CN
5. Setting aside the double bond stereochemistry, what products would you expect from
elimination reactions of the following alkyl halides?
CH3
CI CH3
CH3CHCH2-C-CHCH3
CH3
6. From what alkyl halides are the following alkenes have been made?
CH3
CH3
CH3CHCH2CH2CHCH=CH2
7. Which of the two isomers would you expect to undergo E2 elimination faster? trans-1-bromo-
4-tert-butylcyclohexane or cis-1-bromo-4-tert-butylcyclohexane? Draw each molecule in its
more stable chair conformation. Provide an explanation to your answer.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F8643a326-d31f-4865-abe6-31e0c8793ea8%2F8f08dd63-7f6c-4596-9438-5c9bda6d5099%2Fg9j8bn3_processed.png&w=3840&q=75)
Transcribed Image Text:1. What product is expected to form in an Sn2reaction of OH¯with (R)-2-bromobutane? Show
the stereochemistry of the reactant and the product.
2. What product is expected to form from the Sy2reaction of 1-bromopentane with
а. КОН?
B. NaI?
3. What product would you expect to obtain from a nucleophilic substitution reaction of (S)-2-
bromohexane with CH3 CO7? Assume that inversion configuration occurs, and show the
stereochemistry of both reactant and product?
4. Predict whether each of the following substitution reactions is likely
be SN 1or SN2.
OAc
CH3CO2 Na+
CH3CO2H, H2O
a.
„CH2Br
.CH2OAC
CH3CO2- Na+
DMF
b.
HCI
CI
HO
CH3OH
с.
CH3
CH3
Na+ SCH3
H2C=CCH2SCH3
H2C=CCH2BR
d.
CH3CN
5. Setting aside the double bond stereochemistry, what products would you expect from
elimination reactions of the following alkyl halides?
CH3
CI CH3
CH3CHCH2-C-CHCH3
CH3
6. From what alkyl halides are the following alkenes have been made?
CH3
CH3
CH3CHCH2CH2CHCH=CH2
7. Which of the two isomers would you expect to undergo E2 elimination faster? trans-1-bromo-
4-tert-butylcyclohexane or cis-1-bromo-4-tert-butylcyclohexane? Draw each molecule in its
more stable chair conformation. Provide an explanation to your answer.
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