Solveeit Logo
Login

Question

Question: An organic compound A with molecular formula \({C_3}{H_6}O\) is resistant to oxidation but forms com...

An organic compound A with molecular formula C3H6O{C_3}{H_6}O is resistant to oxidation but forms compound B C3H8O{C_3}{H_8}O on reduction, compound B reacts with HBrHBr form C and C reacts with MgMg from Grignard reagent. D reacts with A to form a product which on hydrolysis gives E. Identify A, B, C, D, E .

Explanation

Solution

The main difference between aldehydes and ketones is that in an aldehyde a hydrogen is attached to the carbon-oxygen double bond while in Ketones there is no such hydrogen attached to the carbon-oxygen double bond.

Complete step by step answer:
In the given question A has formula C3H6O{C_3}{H_6}O which applies to the general formula of ketones and aldehydes which is CnH2nO{C_n}{H_{2n}}O where nn can be any natural number starting from one for aldehydes while for ketones the minimum value of nn must be three so that the first ketone begins with three carbon atom
Now as mentioned in the question A is resistant to oxidation and we all know that ketones does not have any hydrogen attach to the carbon-oxygen double bond making them resistant to oxidation hence the compound A is a ketone having IUPAC name as propan−2−- 2 -one and with common name acetone
Next the compound A on reduction gives B and we all know that ketone give alcohols on reduction hence B having formula C3H8O{C_3}{H_8}O is isopropanol or propan−2−- 2 -ol
Further HBrHBr is added to B which is an alcohol and this is a type of substitution reaction in which O−HO - His replaced by BrBr forming C which is an alkyl halide having formula CH3−CHBr−CH3C{H_3} - CHBr - C{H_3}
Finally C reacts with MgMg obtained from Grignard Reagent to form D which has formula CH3−CHMgBr−CH3   C{H_3} - CHMgBr - C{H_3} \\\ \\\
And we all know that D on reaction with A will form a product that on hydrolysis will form the compound E as stated in the following reaction.

Note:
For oxidation of ketones we need to rupture the C−CC - C bond and thus it’s done with the help of strong oxidizing agent like KMnO4KMn{O_4} or K2Cr2O7{K_2}C{r_2}{O_7} and will produce an ester which on hydrolysis give rise to an alcohol and carboxylic acid.