An organic compound ‘A’ with the molecular formula \(\mathrm{C_6H_4NO_2Br}\) is treated with magnesium in dry ether gives an organometallic compound which on treated with \(\mathrm{CO_2}\) (dry ice) and gives compound ‘B’. ‘B’ on hydrolysis gives ‘C’. The name of the products A and C are
3-nitrobromobenzene and 3-nitrobenzoic acid
\(\mathrm{C_6H_4NO_2Br}\) is a bromonitrobenzene, \(\mathrm{Br{-}C_6H_4{-}NO_2}\); with Mg in dry ether the C–Br bond forms the Grignard reagent \(\mathrm{NO_2C_6H_4MgBr}\).
Grignard reagent + \(\mathrm{CO_2}\) gives the magnesium salt \(\mathrm{NO_2C_6H_4COOMgBr}\) (B); acid hydrolysis gives the carboxylic acid \(\mathrm{NO_2C_6H_4COOH}\) (C), with –COOH where Br was.
The nitro group keeps its position, so A = 3-nitrobromobenzene gives C = 3-nitrobenzoic acid; terephthalic acid or a bromobenzoic acid would need groups that are not present.
Hence, 3-nitrobromobenzene and 3-nitrobenzoic acid.
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Important Questions from Organic Chemistry
- In Dumas method for estimation of nitrogen, 0.50 g of an organic compound gave 70 mL of nitrogen collected at 300 K and 715 mm pressure. The percentage of nitrogen in the organic compound is ______ %.
(Aqueous tension at 300 K is 15 mm). - $0.25 \text{ g}$ of an organic compound "A" containing carbon, hydrogen and oxygen was analysed using the combustion method. There was an increase in mass of $\text{CaCl}_2$ tube and potash tube at the end of the experiment. The amount was found to be $0.15 \text{ g}$ and $0.1837 \text{ g}$, respectively. The percentage of oxygen in compound A is ______ %. (Nearest integer)
(Given: molar mass in $\text{g mol}^{-1}$ $\text{H} : 1, \text{C} : 12, \text{O} : 16$) - Grignard reagent $\text{RMgBr (P)}$ reacts with water and forms a gas $\text{(Q)}$. One gram of Q occupies $1.4 \text{ dm}^3$ at STP. (P) on reaction with dry ice in dry ether followed by $\text{H}_3\text{O}^+$ forms a compound $\text{(Z)}$. 0.1 mole of $\text{(Z)}$ will weigh _________ g. (Nearest integer)
- Consider all the structural isomers with molecular formula $\text{C}_5\text{H}_{11}\text{Br}$ are separately treated with $\text{KOH(aq)}$ to give respective substitution products, without any rearrangement. The number of products which can exhibit optical isomerism from these is ___________.
The major products U and V in the following reaction are
