Chapter 15: Problem 308
When \(10.0 \mathrm{~g}\) of n-propylchloride is allowed to react with excess sodium in the Wurtz reaction, how many grams of hexane would be produced assuming a \(70 \%\) yield?
Chapter 15: Problem 308
When \(10.0 \mathrm{~g}\) of n-propylchloride is allowed to react with excess sodium in the Wurtz reaction, how many grams of hexane would be produced assuming a \(70 \%\) yield?
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Get started for freeAn aromatic dibromide \(\mathrm{C}_{7} \mathrm{H}_{6} \mathrm{Br}_{2}\) reacted with aqueous sodium hydroxide. The product of this reaction had lost only one bromo group to give the product \(\mathrm{C}_{7} \mathrm{H}_{7} \mathrm{BrO}\). When the dibromide was converted to a Grignard reagent and then hydrolyzed, the product was toluene. Determine the structure of the dibromide.
Write balanced equations for the preparation of each of the following organometallic compounds by two different reactions starting from suitable alky1 halides and inorganic reagents. Specify reaction conditions and solvents. In each case, indicate which method of preparation you would prefer from standpoints of yield, convenience, etc. (a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{Zn}\) (c) \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2}\right)_{4} \mathrm{~Pb}\) (b) \(\mathrm{CH}_{3} \mathrm{MgCl}\) (d) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHLi}\)
The following projected synthesis for \(\mathrm{n}\) -butane is not very efficient. Why? \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}+\mathrm{CH}_{3} \mathrm{Br}+2 \mathrm{Na} \rightarrow \mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{2} \mathrm{CH}_{3}+2 \mathrm{NaBr}\)
Excess methylmagnesium iodide and \(0.1776 \mathrm{~g}\) of compound A of formula \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}_{3}\) Sreact to give \(84.1 \mathrm{cc}\) of methane collected over mercury at \(740 \mathrm{~mm}\) and \(25^{\circ} \mathrm{C}\). How many active hydrogens does compound A possess? Suggest a possible structure for the compound given that the infrared spectrum shows no carbonyl absorption and the n.m.r. spectrum shows only three types of hydrogen with areas in the ratio of \(1: 2: 2\).
Write structures for the products of the following reactions involving Grignard reagents. Show the structures of both the intermediate substances and the substances obtained after hydrolysis with dilute acid. Unless otherwise specified, assume that sufficient Grignard reagent is used to cause those reactions to go to completion which occur readily at room temperatures. (a) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{MgBr}+\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHO}\) (b) \(\mathrm{CH}_{3} \mathrm{MgI}+\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{C}_{2} \mathrm{H}_{5}\) (c) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CMgCl}+\mathrm{CO}_{2}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{MgBr}+\mathrm{ClCO}_{2} \mathrm{C}_{2} \mathrm{H}_{5}\) (e) \(\mathrm{CH}_{3} \mathrm{Mg} 1+\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{C}_{2} \mathrm{H}_{5}\) \((1\) mole \()\) \((1\) mole \()\) 0
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