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3. What product would you expect to obtain from a nucleophilic substitution reaction of (S)-2- bromohexane with CH3CO,? Assume that inversion configuration occurs, and show the stereochemistry of both reactant and product?

3. What product would you expect to obtain from a nucleophilic substitution reaction of (S)-2- bromohexane with CH3CO,? Assume that inversion configuration occurs, and show the stereochemistry of both reactant and product?

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter19: Eas: Electrophilic Aromatic Substitution
Section: Chapter Questions
Problem 45E
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3. What product would you expect to obtain from a nucleophilic substitution reaction of (S)-2- bromohexane with CH3CO,? 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 SN1or Sn2. ÇI OAc Only CH3CO2 Na+ CH3CO2H, H2O а. „CH2B CH2OAC CH3CO2- Na+ DMF b. HO. HCI CI CH3OH CH3 CH3 Na+ SCH3 H2C=CCH2B. d. H2C=CCH2SCH3 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. C.
Transcribed Image Text:3. What product would you expect to obtain from a nucleophilic substitution reaction of (S)-2- bromohexane with CH3CO,? 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 SN1or Sn2. ÇI OAc Only CH3CO2 Na+ CH3CO2H, H2O а. „CH2B CH2OAC CH3CO2- Na+ DMF b. HO. HCI CI CH3OH CH3 CH3 Na+ SCH3 H2C=CCH2B. d. H2C=CCH2SCH3 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. C.
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