Functional analysis of aldehydes and ketones

Exercise 4

   

 

An aldehyde function is attached to a saturated unbranched cycle. $2.24\;$ g of the substance $A$ react with excess Tollens reagent in basic medium. Deposition of metallic silver with a mass of $4.316\;g$ is obtained. 1) Calculate the molar mass of the aldehyde. 2) Identify it!

$ n(Ag)$ $=$ $\frac{4.316}{107.9}$ $=$ $0.0400\; mol$ One mole aldehyde gives two moles silver. $ n_A$ $=$ $\frac{0.0400}{2}$ $=$ $0.0200\; mol$ $M_A$ $=$ $\frac{2.24}{0.0200}$ $=$ $112\frac{g}{mol}$ One cycle, one double bond, therefore: General formula: $C_nH_{2n-2}O$ $12n$ $+$ $2n$ $-$ $2$ $+$ $16$ $=$ $112$ $n=7$ Molecular formula: $C_7H_{12}O$ $A$ is cyclohexylmethanal also called (God knows why?) cyclohexylcarbaldehyde.