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Synthesis of an epoxide from 1,2-diol
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+ Stereochemistry
+ Chemistry
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Kevin Baker
Synthesis of an epoxide from 1,2-diol
Thionyl chloride first reacts with the alcohol to form an alkyl chloro sulfite,which gives various stereochemical products as shown here.
Extending this to the current question , alkyl chloro sulfite 2 is formed.${Cl^-}$ attacks in a ${S_N^2}$ mode to give 3.
Base deprotonates 3 to give 4.
Alkoxide and chloride in 4 are in correct trans configuration for a ${S_N^2}$.This results in 5(B in your scheme).
If we take C in your question , and follow the scheme above, 9 is formed.In 9 alkoxide and chloride are not in correct configuration for ${S_N^2}$.Therefore
C in your question does not undergo epoxidation.
Thionyl chloride first reacts with the alcohol to form an alkyl chloro sulfite,which gives various stereochemical products as shown here.
Extending this to the current question , alkyl chloro sulfite 2 is formed.${Cl^-}$ attacks in a ${S_N^2}$ mode to give 3.
Base deprotonates 3 to give 4.
Alkoxide and chloride in 4 are in correct trans configuration for a ${S_N^2}$.This results in 5(B in your scheme).
If we take C in your question , and follow the scheme above, 9 is formed.In 9 alkoxide and chloride are not in correct configuration for ${S_N^2}$.Therefore C in your question does not undergo epoxidation.
Detailed answer but the OP didnt make much of an effort. That is why I offered hints and no answer. Respectfully, I think we should refrain from quickly offering answers when little effort is made by the OP and hints are offered in the comments. Let the OP do some work.More
Thionyl chloride first reacts with the alcohol to form an alkyl chloro sulfite,which gives various stereochemical products as shown here.
Extending this to the current question , alkyl chloro sulfite 2 is formed.${Cl^-}$ attacks in a ${S_N^2}$ mode to give 3.
Base deprotonates 3 to give 4.
Alkoxide and chloride in 4 are in correct trans configuration for a ${S_N^2}$.This results in 5(B in your scheme).
If we take C in your question , and follow the scheme above, 9 is formed.In 9 alkoxide and chloride are not in correct configuration for ${S_N^2}$.Therefore C in your question does not undergo epoxidation.
Thionyl chloride first reacts with the alcohol to form an alkyl chloro sulfite,which gives various stereochemical products as shown here.
Extending this to the current question , alkyl chloro sulfite 2 is formed.${Cl^-}$ attacks in a ${S_N^2}$ mode to give 3.
Base deprotonates 3 to give 4.
Alkoxide and chloride in 4 are in correct trans configuration for a ${S_N^2}$.This results in 5(B in your scheme).
If we take C in your question , and follow the scheme above, 9 is formed.In 9 alkoxide and chloride are not in correct configuration for ${S_N^2}$.Therefore C in your question does not undergo epoxidation.
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