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Chapter 26: Problem 111

Draw the structures of (a) \((E)-3\) -benzyl- 2,5 -dichloro- 4 -methyl- 3 -hexene (b) 1 -ethenyl- 4 -nitrobenzene (c) trans-1-(4-bromophenyl)-2-methylcyclohexane.

Short Answer

Expert verified
The chemical structure of each compound can be drawn based on its name. By understanding the naming of organic compounds, the functional groups and the number of atoms in each molecule, and by following the rules of IUPAC nomenclature, each molecule can be drawn correctly. The drawn structures would show location of all the substituents as well as the correct stereochemistry where necessary (E, trans).

Step by step solution

01

Structure of (E)-3-benzyl-2,5-dichloro-4-methyl-3-hexene

Firstly, identify that this compound is a hexene, meaning it has six carbon atoms and contains a double bond. The double bond is located at the 3rd carbon atom. At the 4th carbon position, there is a methyl group (CH3). There are two chloro molecules at the 2nd and 5th carbon atoms. At the 3rd position, there's a benzene ring (C6H5) attached, which represents a benzyl group. The (E) part of the name indicates the stereochemistry about the double bond, i.e., the priority groups (by atomic number, in this case, the benzyl group and ethyl part of the molecule) are on the opposite sides of the double bond.
02

Structure of 1-ethenyl-4-nitrobenzene

Here, you need to draw a benzene ring. At the 1st position, there is an ethenyl group attached, which is a vinyl group (CH=CH2). At the 4th position, a nitro group (NO2) is attached. So you draw these groups accordingly at the specified positions on the benzene ring.
03

Structure of trans-1-(4-bromophenyl)-2-methylcyclohexane

This compound is a cyclohexane, so you have to draw a cyclohexane ring. At the 1st carbon, a phenyl group (a benzene ring) is attached, which also has a bromine atom at the 4th position of the benzene ring. This means that '4-bromophenyl' is attached at the 1st position of cyclohexane. At the 2nd position of the cyclohexane, a methyl group (CH3) is attached. As the prefix 'trans-' suggests, the bromine atom of the phenyl group and the methyl group are on the opposite sides of the ring.

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Most popular questions from this chapter

The symbol: is often used to represent benzene. It is also the structural formula of cyclohexatriene. Are benzene and cyclohexatriene the same substance? Explain.

Consider the following molecular formulas. How many elements of unsaturation are there in each case? (a) \(\mathrm{C}_{4} \mathrm{H}_{11} \mathrm{N} ;\) (b) \(\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{O} ;\) (c) \(\mathrm{C}_{9} \mathrm{H}_{15} \mathrm{ClO}\).

Classify the carbon atoms in (a) methylbutane, and (b) 2,2 -dimethylpropane as methyl, primary \(\left(1^{\circ}\right)\) secondary \(\left(2^{\circ}\right),\) tertiary \(\left(3^{\circ}\right),\) or quaternary \(\left(4^{\circ}\right)\).

To prepare methyl ethyl ketone, one should oxidize (a) 2-propanol; (a) 1-butanol; (c) 2-butanol; (d) tert-butyl alcohol.

Classify the carbon atoms in (a) 2,4 -dimethylpentane, and (b) ethylcyclobutane as methyl, primary \(\left(1^{\circ}\right)\) secondary \(\left(2^{\circ}\right),\) tertiary \(\left(3^{\circ}\right),\) or quaternary \(\left(4^{\circ}\right)\).
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