a)
Interpretation:
A structure for methyl orange, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.
Concept introduction:
The diazonium cation can act as an electrophile and can attack
To draw:
The structure of methyl orange, an azo dye, produced when the two reactants shown react and to show the electron pushing mechanism for its formation.
b)
Interpretation:
A structure for allura red, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.
Concept introduction:
The diazonium cation can act as an electrophile and attack the aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.
To draw:
The structure of allura red, an azo dye, produced when the two reactants shown react and to give the electron pushing mechanism for its formation.
c)
Interpretation:
A structure for lithol rubine BX, an azo dye, produced when the two reactants shown react is to be drawn and the electron pushing mechanism for its formation is to be shown.
Concept introduction:
The diazonium cation can act as an electrophile and attack the aromatic rings. The dimethylamino group is an o- and p- directing group. Hence the diazonium cation can attack the ring at the p-position to yield a carbocation intermediate. The intermediate then can lose a proton to yield the desired product. This reaction is known as coupling reaction.
To draw:
The structure of lithol rubine BX, an azo dye, produced when the two reactants shown react and to show the electron pushing mechanism for its formation.
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Chapter 16 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
- The following questions concern ethyl (2-oxocyclohexane)carboxylate.(a) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by a Dieckmann cyclization.(b) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by acylation of a ketone.(c) Write structural formulas for the two most stable enol forms of ethyl (2-oxocyclohexane)carboxylate.(d) Write the three most stable resonance contributors to the most stable enolate derived from ethyl (2-oxocyclohexane)carboxylate.(e) Show how you could use ethyl (2-oxocyclohexane)carboxylate to prepare 2-methylcyclohexanone.(f) Give the structure of the product formed on treatment of ethyl (2-oxocyclohexane)-carboxylate with acrolein (H2C=CHCH=O) in ethanol in the presence of sodium ethoxidearrow_forwardDraw the formulas of the reactants and products of the reaction: 2-ethylbutanoyl bromide with excess ethylmagnesium bromide and heating the product with concentrated H2SO4.arrow_forwardAldehydes and ketones react with thiols to yield thioacetals just as they react with alcohols to yield acetals. Predict the product of the following reaction, and propose a mechanism:arrow_forward
- One frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH2N2. The reaction occurs in two steps: (l) protonation of diazomethane by the carboxylic acid to yield methyldiazonium ion, CH3N2+, plus a carboxylate ion; and (2) reaction of the carboxylate ion with CH3N2+. (a) Draw two resonance structures of diazomethane, and account for step 1. (b) What kind of reaction occurs in step 2?arrow_forwardBenzene + nitration, followed by bromination, then reduction of the nitro group to an amine, followed by diazonization, addition of copper I cyanide to the reaction and the product is O benzoyl nitrile O ortho-bromoaniline O para-bromo-nitrobenzene O 3,5-dibromnobenzonitrile O para-bromobenzyl bromidearrow_forwardDraw the structure of each product from the reaction of benzene with 2-chloro-1-methylcyclohexane using AlCl 3 as the catalyst and Identify the major product.arrow_forward
- Provide the major product(s) from the following reaction.arrow_forwardH3C OH OH H+ CH3 Esters can be synthesized by an acid-catalyzed nucleophilic acyl substitution between an alcohol and a carboxylic acid; this process is called the Fischer esterification reaction. Because the alcohol oxygen is a poor nucleophile, the carbonyl carbon is made a better electrophile by protonation of the carbonyl oxygen. The steps of the synthesis are all reversible. The reaction is generally driven to completion by using an excess of the liquid alcohol as a solvent, or by distilling off the product as it forms. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CIX 10-4 H₂O CH3 H₂O CH3arrow_forwardSynthesize p-nitrobenzoic acid from benzene.arrow_forward
- Explain the selectivity observed in the following reactions.arrow_forwardWhat is the structural requirement for a substance to react with ammoniacal AgNO3? Why would acetylene react with Tollen's reagent but not cyclohexane or cyclohexene?arrow_forward22). What is the major product of the following reactions? (A) (B) Br 1) NaCN 2) CH3MgBr 3) H30*/H₂O (C) LOH (D) CNarrow_forward
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