A carboxylic acid with molecular formula, C5H10O2, is treated with thionyl chloride to give compound Z.?
A carboxylic acid with molecular formula, C5H10O2, is treated with thionyl chloride to give compound
Z. Compound Z has only one signal in its 1H NMR spectrum. Provide the IUPAC Name of (or Draw)
the structure of the product that is formed when compound Z is treated with excess ammonia. Having a little trouble starting this one! Thanks!
Answers & Comments
Verified answer
The compound is a carboxylic acid => the formula C5H10O2 can be represented as C4H9COOH
This is reacted with SOCl2.
A carboxylic acid, upon reacting with SOCl2 gives acid chloride - so it the formula of this intermediate would be C4H9COCl.
Upon treating with ammonia this will afford C4H9CONH2.
Now on to the actual structure: hint only ONE peak in the 1H NMR spectrum for the acid chloride => all the protons are equivalent. with four carbon and 9 protons, the only way all the protons will be magnetically equivalent if you have a tert-butyl group. The structure of the intermediate would be (CH3)3C-C(=O)Cl.
The starting material is 2,2,-dimethylpropanoic acid (commonly known as pivalic acid). the intermediate is 2,2-dimethylpropanoyl chloride (also known commonly as pivaloyl chloride) and the final product is 2,2-dimethylpropanamide (also known as Pivalamide).
Hope that helps.
In chemistry, esters are organic compounds in which an organic group (symbolized by R' in this article) replaces a hydrogen atom (or more than one) in an oxygen acid. An oxygen acid is an acid whose molecule has an -OH group from which the hydrogen (H) can dissociate as an H+ ion. The most common esters are the carboxylate esters, where the acid in question is a carboxylic acid. For example, if the acid is acetic acid, the ester is called an acetate. Esters may also be formed with inorganic acids; for example, dimethyl sulfate is an ester, and sometimes called "sulfuric acid, dimethyl ester".