Podcast
Questions and Answers
What is the main role of pyridine in the conversion of alcohols to tosylates?
What is the main role of pyridine in the conversion of alcohols to tosylates?
- It is not involved in the reaction
- It acts as a strong acid
- It acts as a catalyst to speed up the reaction
- It acts as a base to neutralize the acid formed (correct)
What is the abbreviation for the tosyl group?
What is the abbreviation for the tosyl group?
- TOs
- Ts (correct)
- Tos
- TsO
What is the pKa value of p-toluenesulfonic acid (TsOH)?
What is the pKa value of p-toluenesulfonic acid (TsOH)?
- -5
- -9
- -10
- -7 (correct)
What type of mechanism occurs when alkyl tosylates are treated with strong nucleophiles and bases?
What type of mechanism occurs when alkyl tosylates are treated with strong nucleophiles and bases?
What happens to the configuration of the stereogenic center when the leaving group is bonded to it during substitution?
What happens to the configuration of the stereogenic center when the leaving group is bonded to it during substitution?
What is the purpose of converting alcohols to tosylates?
What is the purpose of converting alcohols to tosylates?
What reaction occurs when alkyl tosylates are treated with strong bases?
What reaction occurs when alkyl tosylates are treated with strong bases?
What is required for ethers to undergo substitution or elimination reactions?
What is required for ethers to undergo substitution or elimination reactions?
What type of mechanism is involved in the cleavage of the C-O bond when 2° or 3° alkyl groups are bonded to the ether oxygen?
What type of mechanism is involved in the cleavage of the C-O bond when 2° or 3° alkyl groups are bonded to the ether oxygen?
What is the result of the reaction between ethers and HBr or HI?
What is the result of the reaction between ethers and HBr or HI?
What is the characteristic of the three-membered ring in epoxides that makes nucleophilic attack favorable?
What is the characteristic of the three-membered ring in epoxides that makes nucleophilic attack favorable?
What is the necessary condition for nucleophilic addition to epoxides to occur?
What is the necessary condition for nucleophilic addition to epoxides to occur?
Why do epoxides not contain a good leaving group?
Why do epoxides not contain a good leaving group?
What is the type of mechanism involved in the cleavage of the C-O bond when methyl or 1° R groups are bonded to the ether oxygen?
What is the type of mechanism involved in the cleavage of the C-O bond when methyl or 1° R groups are bonded to the ether oxygen?
What is the mechanism of attack by a nucleophile on an electron-deficient carbon in an epoxide ring?
What is the mechanism of attack by a nucleophile on an electron-deficient carbon in an epoxide ring?
What is the product of the protonation of the alkoxide in the second step of the epoxide ring opening reaction?
What is the product of the protonation of the alkoxide in the second step of the epoxide ring opening reaction?
Which of the following is NOT a common nucleophile that opens an epoxide ring?
Which of the following is NOT a common nucleophile that opens an epoxide ring?
What is the role of acid in the epoxide ring opening reaction with H2O or ROH?
What is the role of acid in the epoxide ring opening reaction with H2O or ROH?
What is the characteristic of the epoxide ring opening reaction with either a strong nucleophile or an acid HZ?
What is the characteristic of the epoxide ring opening reaction with either a strong nucleophile or an acid HZ?
What is the difference in site selectivity between the epoxide ring opening reactions with a strong nucleophile and an acid HZ?
What is the difference in site selectivity between the epoxide ring opening reactions with a strong nucleophile and an acid HZ?
What is the driving force behind the epoxide ring opening reaction?
What is the driving force behind the epoxide ring opening reaction?
What is the role of HCI, HBr, and HI in the epoxide ring opening reaction?
What is the role of HCI, HBr, and HI in the epoxide ring opening reaction?
What is the product of the reaction of an epoxide with an acid HZ?
What is the product of the reaction of an epoxide with an acid HZ?
What is the role of the nucleophile in the first step of the epoxide ring opening reaction?
What is the role of the nucleophile in the first step of the epoxide ring opening reaction?
Which of the following is a common nucleophile that opens an epoxide ring?
Which of the following is a common nucleophile that opens an epoxide ring?
What is the result of the protonation of the alkoxide in the second step of the epoxide ring opening reaction?
What is the result of the protonation of the alkoxide in the second step of the epoxide ring opening reaction?
What is the characteristic of the epoxide ring opening reaction with either a strong nucleophile or an acid HZ?
What is the characteristic of the epoxide ring opening reaction with either a strong nucleophile or an acid HZ?
What is the difference between the site selectivity of the epoxide ring opening reactions with a strong nucleophile and an acid HZ?
What is the difference between the site selectivity of the epoxide ring opening reactions with a strong nucleophile and an acid HZ?
Which of the following acids can open an epoxide ring?
Which of the following acids can open an epoxide ring?
What is the role of water in the epoxide ring opening reaction with an acid HZ?
What is the role of water in the epoxide ring opening reaction with an acid HZ?
Why do strong nucleophiles open an epoxide ring?
Why do strong nucleophiles open an epoxide ring?
What is the mechanism of the first step of the epoxide ring opening reaction?
What is the mechanism of the first step of the epoxide ring opening reaction?
What is the driving force behind the relief of the strain of the three-membered ring?
What is the driving force behind the relief of the strain of the three-membered ring?
The epoxide ring opening reaction with a strong nucleophile is a one-step reaction.
The epoxide ring opening reaction with a strong nucleophile is a one-step reaction.
Acids such as HCl, HBr, and HI can open an epoxide ring.
Acids such as HCl, HBr, and HI can open an epoxide ring.
The site selectivity of the epoxide ring opening reactions with a strong nucleophile and an acid HZ is the same.
The site selectivity of the epoxide ring opening reactions with a strong nucleophile and an acid HZ is the same.
NH3 is a common nucleophile that opens an epoxide ring.
NH3 is a common nucleophile that opens an epoxide ring.
The epoxide ring opening reaction is non-regioselective.
The epoxide ring opening reaction is non-regioselective.
The three-membered ring in epoxides is strain-free.
The three-membered ring in epoxides is strain-free.
Water is not involved in the epoxide ring opening reaction with an acid HZ.
Water is not involved in the epoxide ring opening reaction with an acid HZ.
The alkoxide is not protonated in the second step of the epoxide ring opening reaction.
The alkoxide is not protonated in the second step of the epoxide ring opening reaction.
The epoxide ring opening reaction with a strong nucleophile is a reversible reaction.
The epoxide ring opening reaction with a strong nucleophile is a reversible reaction.
ROH can open an epoxide ring in the presence of acid.
ROH can open an epoxide ring in the presence of acid.
