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
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- A step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.arrow_forwardA graduate student tried to make o-fluorophenylmagnesium bromide by adding magnesium to an ether solution of o-fluorobromobenzene. After obtaining puzzling results with this reaction, she repeated the reaction by using as solvent some tetrahydrofuran that contained a small amount of furan. From this reaction, she isolated a fair yield of the compound that follows. Propose a mechanism for its formation.arrow_forward
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