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Chapter 12: Problem 247

Provide the missing reactant or reaction condition for the following: (a) \(\mathrm{n}\) -heptane \(+\underline{\text { ? }}\) * toluene (b) Iodobenzene \(+\underline{?}\) biphenyl (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COCH}_{3}+?\) \+ ethyl benzene

Short Answer

Expert verified
The missing reactants and reaction conditions for each reaction are: (a) \(\mathrm{CH_3Cl}\) and \(\mathrm{AlCl_3}\) (b) \(\mathrm{Mg}\) and ether (c) \(\mathrm{H_2}\) and \(\mathrm{Pd/C}\)

Step by step solution

01

In this reaction, we need to add a reactant which can lead to the formation of toluene. This means we need to remove a hydrogen molecule from n-heptane and substitute it with a methyl group. For this transformation, we need a reagent that can promote the necessary substitution. #Step 2: Determine the missing reactant for n-heptane and toluene#

A reagent that can be used for this purpose is chloromethane (\(\mathrm{CH_3Cl}\)), in the presence of a catalyst such as aluminum chloride (\(\mathrm{AlCl_3}\)). The reaction can be written as: \[\text{n-heptane} + \mathrm{CH_3Cl} \xrightarrow{\mathrm{AlCl_3}} \text{toluene}\] #Step 3: Identify the reaction for Iodobenzene and biphenyl#
02

In this reaction, we need to add a reactant which can lead to the formation of biphenyl. This means we need to couple two phenyl rings together. For this transformation, we need a reagent that can promote the necessary coupling. #Step 4: Determine the missing reactant for Iodobenzene and biphenyl#

A reagent that can be used for this purpose is magnesium metal (\(\mathrm{Mg}\)), in the presence of a suitable solvent like ether. This is a typical example of a Grignard reaction. The reaction can be written as: \[\text{iodobenzene} + \mathrm{Mg} \xrightarrow{\text{ether}} \text{biphenyl}\] #Step 5: Identify the reaction for \(\mathrm{C_6H_5COCH_3}\) and ethyl benzene#
03

In this reaction, we need to add a reactant which can lead to the formation of ethyl benzene. This means we need to remove an \(\mathrm{COCH_3}\) group from the given reactant and replace it with a hydrogen atom. For this transformation, we need a reagent that can promote the necessary reduction and replacement. #Step 6: Determine the missing reactant for \(\mathrm{C_6H_5COCH_3}\) and ethyl benzene#

A reagent that can be used for this purpose is hydrogen gas (\(\mathrm{H_2}\)), in the presence of a catalyst such as palladium (\(\mathrm{Pd}\)) on carbon. The reaction can be written as: \[\text{\(\mathrm{C_6H_5COCH_3}\)} + \mathrm{H_2} \xrightarrow{\mathrm{Pd/C}} \text{ethyl benzene}\] So, the missing reactants and reaction conditions are as follows: a) \(\mathrm{CH_3Cl}\) and \(\mathrm{AlCl_3}\) b) \(\mathrm{Mg}\) and ether c) \(\mathrm{H_2}\) and \(\mathrm{Pd/C}\)

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Most popular questions from this chapter

Draw the structure of: (a) \(\mathrm{m}\) -xylene (g) isopropylbenzene (cumene) (b) mesitylene (h) trans-stilbene (c) o-ethyltoluene (i) 1,4 -diphenyl-1,3-butadiene (d) \(p\) -di-tert-butylbenzene (j) p-dibenzylbenzene (e) cyclohexylbenzene (k) m-bromos tyrene (f) 3-phenylpentane (1) diphenylacetylene

Suggest possible routes for the synthesis of the following compounds:

Describe simple chemical tests that would distinguish between: (a) benzene and toluene; (b) bromobenzene and bromocyclohexane; (c) bromobenzene and 3 -bromo-1-hexene: (d) ethylbenzene and benzyl alcohol \(\left(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{OH}\right)\).

What would you predict for the general character of the chemical shifts of the protons of (a) the separate \(\mathrm{CH}_{2}\) groups of 1,4 -hexamethylenebenzene as compared with 1,2 -hexamethylenebenzene; 1,4 -hexamethylenebenzene 1,2 -hexamethylenebenzene (b) cyclodctatetraene

Give structures and names of the principal organic products expected from the reaction of n-propylbenzene with each of the following: (1) \(\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}, \mathrm{H}_{2} \mathrm{SO}_{4}\), heat (3) \(\mathrm{Cl}_{2}, \mathrm{Fe}\) (2) \(\mathrm{HNO}_{3}, \mathrm{H}_{2} \mathrm{SO}_{4}\) (4) \(\mathrm{Br}_{2}\), heat, light (5) cyclohexene, \(\mathrm{HF}\)
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