Q 3-3-50 E - Organic Chemistry (Mcmurry)

Question

Formaldehyde, ${\mathrm{H}}_2\mathrm{C}=\mathrm{O}$, is known to all biologists because of its usefulness as a tissue preservative. When pure, formaldehyde trimerizes to give trioxane, ${\mathrm{C}}_3{\mathrm{H}}_6{\mathrm{O}}_3$, which, surprisingly enough, has no carbonyl groups. Only one monobromo derivative (${\mathrm{C}}_3{\mathrm{H}}_5{\mathrm{BrO}}_3$) of trioxane is possible. Propose a structure for trioxane.

Step-by-Step Solution

Answer

Trioxane structure is:

Formaldehyde

Its an aldehyde the molecule formula is HCHO that means its is the first aldehyde when it trimerise means when three molecule of formaldehyde join together.

Trimerisation of Formaldehyde

When the three molecules of f formaldehyde join together to form the new structure that is trioxane having molecular formula ${\mathrm{C}}_3{\mathrm{H}}_6{\mathrm{O}}_3$ it means that no atoms are eliminated while joining and all the original atoms are present.

No carbonyl group

No carbonyl group is present in the trioxane means only oxygen-containing functional group is present are ethers or alcohols

Mono bromo derivative

Trioxane forms only mono bromo derivate means that only 1 H is replaced by the Br group the only one type of hydrogen is present in the group.

Structure of Trioxane

Hence, from all the above steps the structure of trioxane must be as follows: