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Chapter 27: Problem 69

The three isomeric tribromobenzenes, I, II, and III, when nitrated, form three, two, and one mononitrotribromobenzenes, respectively. Assign correct structures to I, II, and III.

Short Answer

Expert verified
The structures of isomeric tribromobenzenes I, II, and III are 1,2,3-tribromobenzene, 1,2,4-tribromobenzene, and 1,3,5-tribromobenzene, respectively.

Step by step solution

01

Understand the concept of isomers and nitration

Isomers are compounds with the same molecular formula but different structural arrangements. In this case, tribromobenzenes will have the same molecular formula with different positions for bromine atoms. Nitration is a chemical process that introduces a nitro group into a molecule. For benzene ring, nitration will occur at positions ortho, meta or para relative to bromine atoms.
02

Derive possible isomers of tribromobenzenes

The three possible isomers for tribromobenzenes, based on the positions of bromine atoms, are 1,2,3-tribromobenzene (with bromine atoms at adjacent positions), 1,2,4-tribromobenzene (with a bromine atom at an ortho and para to another), and 1,3,5-tribromobenzene (bromine atoms occupy alternate positions).
03

Determine the possible nitration sites for each isomer and match with the information given

The 1,2,3-tribromobenzene can be nitrated at three different positions while 1,2,4-tribromobenzene can be nitrated at two positions, and 1,3,5-tribromobenzene can only be nitrated at one unique position. Matching this information with the given exercise, tribromobenzenes I, II, and III can be identified as 1,2,3-tribromobenzene, 1,2,4-tribromobenzene, and 1,3,5-tribromobenzene, respectively.
04

Establish and verify the structures of the isomers

Draw the structures of I, II, and III, and verify by cross-checking with nitration sites. Isomer I (1,2,3-tribromobenzene) has three possible nitration spots making it yield three products. Isomer II (1,2,4-tribromobenzene) has two possible nitration sites producing two products. Isomer III (1,3,5-tribromobenzene) has one unique nitration spot producing one product.

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Most popular questions from this chapter

Answer the following questions for this \(S_{\mathrm{N}} 2\) reaction: $$\begin{aligned} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}+\mathrm{NaOH} & \longrightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}+ \mathrm{NaBr} \end{aligned}$$ (a) What is the rate expression for the reaction? (b) Draw the reaction profile for the reaction. Label all parts. Assume that the products are lower in energy than the reactants. (c) What is the effect on the rate of the reaction of doubling the concentration of \(n\) -butyl bromide? (d) What is the effect on the rate of the reaction of halving the concentration of sodium hydroxide?

For the monochlorination of hydrocarbons, the following ratio of reactivities has been found: \(3^{\circ}>2^{\circ}>\) \(1^{\circ}, \quad 4.3: 3: 1 . \quad\) How many different monochloro derivatives of 2 -methylbutane are possible, and what percentage of each would you expect to find?

Answer the following questions for this E1 reaction: $$\begin{array}{c} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{Br}+\mathrm{CH}_{3} \mathrm{OH} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}=\mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}+\mathrm{Br}^{-}+\mathrm{CH}_{3} \mathrm{OH}_{2}^{+} \end{array}$$ (a) What is the rate expression for the reaction? (b) Draw the reaction profile for the reaction. Label all parts. Assume that the products are lower in energy than the reactants. (c) What is the effect on the rate of the reaction of doubling the concentration of \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{Br} ?\) (d) What is the effect on the rate of the reaction of doubling the concentration of \(\mathrm{CH}_{3} \mathrm{OH} ?\)

A sample of \((R)-\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{Cl}\) reacts with \(\mathrm{CH}_{3} \mathrm{O}^{-}\) in dimethyl sulfoxide, \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{SO},\) a convenient solvent for organic reactions. The resulting solution is optically active. (a) Write the formula of the product. (b) By which mechanism does this nucleophilic substitution reaction occur?

Which of the following reactions would give a better yield of \(\mathrm{CH}_{3} \mathrm{OCH}\left(\mathrm{CH}_{3}\right)_{2} ?\) Explain. \(\mathrm{CH}_{3} \mathrm{ONa}+\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHI} \longrightarrow \mathrm{CH}_{3} \mathrm{OCH}\left(\mathrm{CH}_{3}\right)_{2}+\mathrm{NaI}\) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHONa}+\mathrm{CH}_{3} \mathrm{I} \longrightarrow \mathrm{CH}_{3} \mathrm{OCH}\left(\mathrm{CH}_{3}\right)_{2}+\mathrm{NaI}\)
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