Holooly Plus Logo
Holooly Plus Logo

Question 16.60: The following compound isomerizes in aqueous NaOH to give a ......

The following compound isomerizes in aqueous NaOH to give a tetrahydropyran. What is the structure of the product? Write a mechanism for its formation.

لقطة الشاشة 2023-08-15 195921
Step-by-Step
The 'Blue Check Mark' means that this solution was answered by an expert.
Learn more on how do we answer questions.
Report Answer

The alkoxide ion formed by proton exchange with base is a nucleophile. It attacks the primary carbon atom of the epoxide to open the three-membered ring. The result of the intramolecular substitution reaction is a six-membered ring.

Related Answered Questions

Question: 16.19

Draw the stable conformation of 1,4-dioxane. ...

Verified Answer:

Question: 16.62

Deduce the structure of a compound with the molecular formula C₄H₈O based on the following proton NMR spectrum plus the information that the 1³C NMR spectrum has two peaks whose chemical shifts are 30 and 45 ppm. ...

Verified Answer:

The formula of the compound tells us that it is a ...
Question: 16.57

The reaction of (2S,3R)-2,3-dimethyloxirane with aqueous acid gives a mixture of enantiomers. Explain why a mixture is obtained. What are the configurations of all stereogenic centers of both isomers? ...

Verified Answer:

The reaction occurs with inversion of configuratio...
Question: 16.58

The reaction of (2R,3R)-2,3-dimethyloxirane with aqueous acid gives a single optically inactive product. Explain the origin of this product. What are the configurations of all stereogenic centers of the product? ...

Verified Answer:

The reaction occurs with inversion of configuratio...
Question: 16.59

Sodium ethoxide in ethanol reacts with 1-(chloromethyl)oxirane containing a 14C label at the position shown by the asterisk. Write a two-step mechanism that explains why the label is at the indicated position in the product. ...

Verified Answer:

Ring opening of the epoxide as the result of nucle...
Question: 16.61

Deduce the structure of a compound with the molecular formula C₄H₆Cl₂O based on the following proton NMR spectrum. ...

Verified Answer:

The spectrum contains a low-field singlet at ~5 d ...
Question: 16.52

The reaction of methyllithium with an epoxide followed by neutralization gives an alcohol. Write the product of the reaction of cyclohexene oxide with methyl lithium, showing the structure in its most stable conformation. ...

Verified Answer:

Reaction of the methyl carbanion inverts the confi...
Question: 16.53

Write the structure of the amino alcohol formed in the reaction of (2S,3R)-2,3-dimethyloxirane with aqueous ammonia. Explain why this compound forms in preference to a diol. Assign the stereochemistry of each chiral center in the product. ...

Verified Answer:

Ammonia is a better nucleophile than water. The re...
Question: 16.54

Epoxide rings can be cleaved by phenoxides. Propose a synthesis of the muscle relaxant methocarbamol using this fact. ...

Verified Answer:

A ring opening reaction of the following epoxide a...
Question: 16.55

A mixture of 2,2-dimethyloxirane and ethanethiol is treated with sodium hydroxide. Write the structure of the expected product. ...

Verified Answer:

The ring opening reaction of the epoxide by the nu...