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Chapter 15: Q22P (page 477)

Draw and name all possible aromatic compounds with the formula C8H9Br.

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01

Step-by-Step SolutionStep 1: Aromatic compounds

There is a possibility of many isomers for the molecular formula C8H9Bras it has a benzene ring followed by two extra carbon which can be present in the form of methyl as a substituent and bromine group.

02

 All possible structures and their name

All possible aromatic compounds with the formulaC8H9Br are as follows:

(V)1-bromo-3,5-dimethylbenzene (VI)3-bromoethyltoulene

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Most popular questions from this chapter

Look at the five resonance structures for phenanthrene (Problem 15-26), and predict which of its carbon-carbon bonds is the shortest.

Propose structures for compounds that fit the following descriptions:

(a) C10H141HNMR: 7.18鈥�未(4 H, broad singlet);2.70鈥�未(4 H, quartet, J = 7 Hz); 1.20鈥�未(6 H, triplet, J =7 Hz) IR:745鈥�cm-1.

(b)C10H141HNMR:7.0鈥�未(4 H, broad singlet);2.85鈥夆赌�未(1 H, septet, J = 8 Hz);2.28鈥夆赌�未(3 H, singlet);1.20鈥夆赌�未(6 H, doublet, J = 8 Hz) IR:825鈥�cm-1.

Cyclopropane is highly reactive because of its large amount of angle strain. Methylcyclopropenone, although even more strained than cyclopropanone, is nevertheless quite stable and can even be distilled. Explain, taking the polarity of the carbonyl group into account.

Cyclopropanone Methylcyclopropenone

Pyridine is a flat, hexagonal molecule with bond angles of 120掳. It undergoes substitution rather than addition and generally behaves like benzene. Draw a picture of the orbitals of pyridine to explain its properties. Check your answer by looking ahead to Sections 15-5.

Draw structures corresponding to the following names:

(a) 3-Methyl-1,2-benzenediamine

(b) 1,3,5-Benzenetriol

(c) 3-Methyl-2-phenylhexane

(d) o-Aminobenzoic acid

(e) m-Bromophenol

(f) 2,4,6-Trinitrophenol (picric acid)
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