Question: Draw the substitution product formed (including stereochemistry) when (R)-hexan-2-ol is treated with each series of reagents: (a) NaH, followed by ; (b) TsCl and pyridine, followed by ; (c) , followed by . Which two routes produce identical products?
Route (a) and route (c) produces identical products.
Alcohols can get subjected to nucleophilic substitution reactions or elimination reactions if the OH group is transformed into an excellent leaving group. This can be done with the help of acids.
The spatial organization of various atoms can be investigated using stereochemistry. Chiral molecules can be analyzed using stereochemistry.
a. The reaction of (R)-hexan-2-ol with NaH and does not lead to a change in configuration and the reaction can be given as:
The reaction of (R)-hexan-2-ol with NaH and
b. The reaction of (R)-hexan-2-ol with TsCl and pyridine, followed by leads to a change in configuration and the reaction can be given as:
The reaction of (R)-hexan-2-ol with TsCl and pyridine, followed by
c. The reaction of (R)-hexan-2-ol with followed by does not lead to a change in configuration and the reaction can be given as:
The reaction of followed by
The products produced in reactions a and c are (R)-2-methoxyhexane. Hence, routes (a) and (c) produces identical products.
Question: Aziridines are heterocycles that contain an N atom in a three-membered ring. Like epoxides, aziridines are strained and reactive because the 60° bond angles of the three-membered ring deviate greatly from the theoretical tetrahedral bond angle. One step in the synthesis of the drug oseltamivir (trade name Tamiflu, Section 3.2) involves the conversion of amine X to diamine Y, a reaction that occurs by way of an intermediate aziridine. Draw a stepwise mechanism for the conversion of X to Y. Indicate the structure of the aziridine intermediate, and explain the trans stereochemistry of the two amines in Y
Question: 1,2-Diols are converted to carbonyl compounds when treated with strong acids, in a reaction called the pinacol rearrangement.
(a) Draw a stepwise mechanism for this reaction. (Hint: The reaction proceeds by way of carbocation intermediates.)
(b) Assuming that the pinacol rearrangement occurs via the more stable carbocation, draw the rearrangement product formed from diol D.
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