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Reaction of \(1,2,3\) -tribromo-5-nitrobenzene with sodium ethoxide in ethanol gave a single product, \(\mathrm{C}_{8} \mathrm{H}_{7} \mathrm{Br}_{2} \mathrm{NO}_{3}\), in quantitative yield. Suggest a reasonable structure for this compound.

Short Answer

Expert verified
The structure is 1,2-dibromo-3-ethoxy-5-nitrobenzene.

Step by step solution

01

Identify the Initial Structure

The starting compound is 1,2,3-tribromo-5-nitrobenzene. This means our benzene ring has three bromine ( Br) groups at positions 1, 2, and 3, and a nitro ( NO_2) group at position 5.
02

Consider Reagent Action

Sodium ethoxide in ethanol is a strong base and good nucleophile. It likely facilitates a nucleophilic aromatic substitution by replacing one of the bromine atoms in 1,2,3-tribromo-5-nitrobenzene.
03

Determine Site of Substitution

The presence of the nitro group, an electron-withdrawing group, at position 5 will activate positions ortho and para to it for nucleophilic aromatic substitution. Thus, the bromine at position 3, ortho to the nitro group, is the most reactive and will be replaced by the ethoxide group.
04

Predict Product Structure

After substitution, the product will have bromines at positions 1 and 2, an ethoxy group ( OC_2H_5 ) at position 3, and the nitro group at position 5, resulting in 1,2-dibromo-3-ethoxy-5-nitrobenzene.
05

Verify Molecular Formula

The proposed structure is 1,2-dibromo-3-ethoxy-5-nitrobenzene. Confirm the molecular formula: C_8 H_7 Br_2 NO_3 , which matches our requirement of C_8 H_7 Br_2 NO_3.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Tribromo-nitrobenzene
Understanding the structure of tribromo-nitrobenzene is essential to grasp the reaction mechanism in nucleophilic aromatic substitution. Here, we start with a benzene ring, which is an aromatic compound known for its stability due to conjugated double bonds. In this derivative, the benzene ring is substituted with three bromine (Br) atoms and one nitro (NO鈧) group.
  • The term '1,2,3-tribromo' indicates that bromine atoms are located at the first, second, and third positions on the benzene ring.
  • The '5-nitro' part means a nitro group (NO鈧) is attached to the fifth position.
This structure introduces an element of asymmetry, which is important when considering chemical reactions. The multiple bromine substituents and the nitro group influence the reactivity of the compound. Specifically, the nitro group is an electron-withdrawing group, which makes the benzene ring more susceptible to attack by nucleophiles at positions ortho and para to the nitro group.
Sodium Ethoxide
Sodium ethoxide, represented chemically as NaOEt, plays a crucial role as a reagent in this reaction. It is known as a strong base and an effective nucleophile. In the context of nucleophilic aromatic substitution, sodium ethoxide performs the following roles:
  • Base Action: NaOEt can deprotonate molecules, but in this particular reaction, its role is primarily that of a nucleophile.
  • Nucleophilic Action: The ethoxide ion (EtO鈦) generated from sodium ethoxide can attack the carbon atom bearing a leaving group, leading to the substitution.
Typically, nucleophilic aromatic substitution isn't as common as its electrophilic counterpart. However, the presence of electron-withdrawing groups like nitro (NO鈧) on the benzene ring significantly increases the ring's susceptibility to this type of reaction. Thus, sodium ethoxide replaces a bromine atom in the tribromo-nitrobenzene.
Benzene Derivatives
Benzene derivatives are central to understanding many organic reactions, due to their stability and versatility in undergoing substitution reactions. The reactivity of a benzene derivative can be tailored by altering the substituents on the ring.
  • Aromatic Stability: Benzene derivatives maintain the characteristic stability of benzene due to delocalized electrons in their ring structure.
  • Substituent Effects: Adding groups like bromine and nitro impacts the electron density of the ring, influencing reactivity.
    • Electron-Withdrawing: Nitro groups pull electron density away, enhancing reactivity to nucleophiles.
    • Leaving Groups: Bromine is a good leaving group, facilitating substitution reactions.
In the context of the reaction, the transformation of 1,2,3-tribromo-5-nitrobenzene to a dibromo-ethoxy-nitrobenzene product exemplifies how substituents control reactivity and product formation in benzene derivatives. Consideration of these factors is essential when predicting product structures and understanding reaction mechanisms.

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Most popular questions from this chapter

In each of the following pairs of compounds choose which one will react faster with the indicated reagent, and write a chemical equation for the faster reaction: (a) Toluene or chlorobenzene with a mixture of nitric acid and sulfuric acid (b) Fluorobenzene or (trifluoromethyl)benzene with benzyl chloride and aluminum chloride Linear low-density polyethylene is a copolymer in which ethylene is polymerized under Ziegler-Natta conditions in the presence of a smaller quantity of a second alkene such as 1-hexene. What structural feature characterizes the resulting polymer?

Arrange the following five compounds in order of decreasing rate of bromination: benzene, toluene, \(o\) -xylene, \(m\) -xylene, \(1,3,5\) -trimethylbenzene (the relative rates are \(2 \times 10^{7}, 5 \times 10^{4}, 5 \times 10^{2}, 60\), and 1).

Write equations showing how to prepare each of the following from benzene or toluene and any necessary organic or inorganic reagents. If an ortho, para mixture is formed in any step of your synthesis, assume that you can separate the two isomers. (a) Isopropylbenzene (b) \(p\) -Isopropylbenzenesulfonic acid (c) 2-Bromo-2-phenylpropane (d) 4-tert-Butyl-2-nitrotoluene (e) \(m\) -Chloroacetophenone (f) \(p\) -Chloroacetophenone (g) 3-Bromo-4-methylacetophenone (h) 2-Bromo-4-ethyltoluene (i) 3-Bromo-5-nitrobenzoic acid (j) 2-Bromo-4-nitrobenzoic acid (k) 1-Phenyloctane (1) 1-Phenyl-1-octene (m) 1-Phenyl-1-octyne (n) 1,4 -Di-tert-butyl- 1,4 -cyclohexadiene

Nitration of 1,4 -dimethylbenzene (p-xylene) gives a single product having the molecular formula \(\mathrm{C}_{\mathrm{a}} \mathrm{H}_{9} \mathrm{NO}_{2}\) in high yield. What is this product?

Reaction of hexamethylbenzene with methyl chloride and aluminum chloride gave a salt A, which, on being treated with aqueous sodium bicarbonate solution, yielded compound B. Suggest a mechanism for the conversion of hexamethylbenzene to \(\mathrm{B}\) by correctly inferring the structure of \(\mathrm{A}\).

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