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Draw structures of: (a) p-dinitrobenzene (b) \(\mathrm{m}\) -bromoni trobenzene (c) o-chlorobenzoic acid (d) \(\mathrm{m}\) -nitrotoluene (e) \(\mathrm{p}\) -bromoaniline (f) \(\mathrm{m}\) -iodophenol (g) mesitylene \((1,3,5\) -tri- methylbenzene) (h) 3,5 -dinitrobenzenesulfonic acid (i) 4-chloro-2,3-dinitrotoluene (j) 2 -amino-5-bromo-3-nitro- benzoic acid (k) p-hydroxyberizoic acid (1) \(2,4,6\) -trinitrophenol (picric acid)

Short Answer

Expert verified
#tag_title# (b) m-bromonitrobenzene #tag_content# Begin by drawing a benzene ring. Next, add a bromine atom (Br) at the 1 position, and a nitro group (\( NO_2 \)) at the 3 (meta) position on the ring.

Step by step solution

01

(a) p-dinitrobenzene

To draw the structure of p-dinitrobenzene, start by drawing a benzene ring. Then, add two nitro groups (\( NO_2 \)) at the 1 (or para) and 4 positions on the benzene ring.

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Key Concepts

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

p-Dinitrobenzene Structure
When attempting to visualize the structure of p-dinitrobenzene, imagine first the foundation: a hexagonal benzene ring which is the hallmark of aromatic hydrocarbons. The 'p' in p-dinitrobenzene stands for para, indicating the relative positions of the substituent groups on the benzene ring.

In this case, we have two nitro groups ((NO_2)), which consist of a nitrogen atom bonded to two oxygen atoms. These nitro groups are attached to opposite sides of the benzene ring—that is, they are para to each other. This means they are located on the number 1 and number 4 carbon atoms of the ring. The full structure is then completed by adding the hydrogen atoms to the remaining carbon atoms of the benzene ring that are unoccupied by the nitro groups.

Understanding the concept of 'para' positioning is essential, as it dictates the behavior and properties of this compound. Para-substituted benzene derivatives often have distinct chemical and physical characteristics, and knowing the structure is crucial for predicting reactivity and interactions with other substances in chemical reactions.
Organic Chemistry Nomenclature
Nomenclature in organic chemistry is like a detailed map, guiding you through the complex maze of organic compounds. It's vital for clear communication and understanding within the scientific community. To name organic compounds, there are established rules set by the International Union of Pure and Applied Chemistry (IUPAC).

Let's break it down using p-dinitrobenzene as an example. The name begins with a prefix 'p-', indicating that the substituent groups are para to each other. The 'di-' signals that there are two nitro groups. Then, 'nitro' specifies the type of substituent, and 'benzene' denotes the core aromatic ring structure.

Whether you are dealing with simple molecules or complex structures, mastering the IUPAC nomenclature ensures that you can both identify and articulate organic compounds accurately. It's an essential skill for students and professionals in chemistry and related scientific fields.
Benzene Derivatives
Benzene derivatives form a diverse family of compounds that are essential in both nature and industry. They're derived from benzene, an aromatic hydrocarbon with a six-carbon ring and alternating double bonds. The unique stability of benzene forms the backbone of these derivatives.

A benzene derivative is created when one or more hydrogen atoms from the benzene ring are replaced with other atoms or groups of atoms, known as substituents. These compounds are omnipresent in chemical synthesis, pharmaceuticals, and materials science.

For instance, adding different substituents and their arrangements like the para, meta, or ortho positions on the benzene ring can dramatically alter the physical properties and reactivity of the molecule. The versatility of benzene derivatives stems from the various substituents that provide a range of properties and applications, making them a cornerstone of organic chemistry.

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Most popular questions from this chapter

For which of the following might you expect aromaticity (geometry permitting)? (a) The annulenes containing up to 20 carbons. (Annulenes are monocyclic compounds of the general formula \([-\mathrm{CH}=\mathrm{CH}-]_{\mathrm{n}}\). (b) The monocyclic polyenes \(\mathrm{C}_{9} \mathrm{H}_{10} \mathrm{C}_{9} \mathrm{H}_{9}^{+}, \mathrm{C}_{9} \mathrm{H}_{9}{ }^{-}\).

For a time the prism formula VI, proposed in 1869 by Albert Ladenburg of Germany, was considered as a possible structure for benzene, on the grounds that it would yield one monosubstitution product and three isomeric disubstitution products. (a) Draw Ladenburg structures of three possible isomeric dibromobenzenes. (b) On the basis of the Korner method of absolute orientation, label each Ladenburg structure in (a) as ortho, meta, or para. (c) Can the Ladenburg formula actually pass the test of isomer number? (Derivatives of Ladenburg "benzene," called prismanes, have actually been made.)

Biphenyl, \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{C}_{6} \mathrm{H}_{5}\), has a conjugation energy of 71 \(\mathrm{kcal} / \mathrm{mole}\) (a) Draw an atomic orbital picture of biphenyl, (b) What are its most important resonance contributing structures? (c) Estimate the heat of hydrogenation of biphenyl.

When benzene is treated with chlorine under the influence of ultraviolet light, a solid material of \(\mathrm{m}\). wt. 291 is formed. Quantitative analysis gives an empirical formula of \(\mathrm{CHC} 1 .\) (a) What is the molecular formula of the product? (b) What is a possible structural formula? (c) What kind of reaction has taken place? (d) Is the product aromatic? (e) Actually, the product can be isolated into six isomeric compounds, one of which is used as an insecticide (Gammexane or Lindane). How do these isomers differ from each other? (f) Are more than six isomers possible?

\(1,3,5,7-\) Cyclooctatetraene, \(\mathrm{C}_{8} \mathrm{H}_{8}\), has a heat of combustion of \(1095 \mathrm{kcal} ;\) it rapidly decolorizes cold aqueous \(\mathrm{KMnO}_{4}\), and reacts with \(\mathrm{Br}_{2} / \mathrm{CCl}_{4}\), to yield \(\mathrm{C}_{8} \mathrm{H}_{8} \mathrm{Br}_{8}\). (a) How should its structure be represented? (b) Upon what theoretical grounds might one have predicted its structure and properties? (c) Treatment of cyclooctatetraene with potassium metal has been found to yield a stable compound \(2 \mathrm{~K}^{+} \mathrm{C}_{8} \mathrm{H}_{8}{ }^{--}\) Of what significance is the formation of this salt? (d) Using models, suggest a possible shape (or shapes) for cyclooctatetraene. What shape would you predict for the \(\mathrm{C}_{8} \mathrm{H}_{8}^{--}\) anion?

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