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Chapter 3: Problem 17

Draw the structures for 1,4 -cyclohexadiene, \(1,3,5,7\)-cyclooctatetraene, 5 -methyl-1,3-cyclohexadiene, 2 -fluoro-1,3-cyclohexadiene, 3-bromo-1,4cycloheptadiene, and 1-bromo-1,4-cycloheptadiene.

Short Answer

Expert verified
Draw the base rings first and then add the double bonds and substituent groups as specified in each molecular structure.

Step by step solution

01

- Draw the structure of 1,4-cyclohexadiene

Start with the cyclohexane ring, which is a six-membered ring. Add double bonds at the 1 and 4 positions.
02

- Draw the structure of 1,3,5,7-cyclooctatetraene

Draw an eight-membered ring which is the cyclooctane structure. Add double bonds at the 1, 3, 5, and 7 positions.
03

- Draw the structure of 5-methyl-1,3-cyclohexadiene

Draw a six-membered cyclohexane ring. Add double bonds at the 1 and 3 positions. Finally, attach a methyl group (CH3) at the 5 position.
04

- Draw the structure of 2-fluoro-1,3-cyclohexadiene

Draw a six-membered cyclohexane ring. Add double bonds at the 1 and 3 positions. Then attach a fluorine atom (F) at the 2 position.
05

- Draw the structure of 3-bromo-1,4-cycloheptadiene

Draw a seven-membered cycloheptane ring. Add double bonds at the 1 and 4 positions. Lastly, attach a bromine atom (Br) at the 3 position.
06

- Draw the structure of 1-bromo-1,4-cycloheptadiene

Draw a seven-membered cycloheptane ring. Add double bonds at the 1 and 4 positions. Attach a bromine atom (Br) at the 1 position.

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Key Concepts

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

Cyclohexadiene
Cyclohexadiene is a cycloalkene with the formula \(C_6H_8\). It consists of a six-membered ring (cyclohexane) with two double bonds. The positions of these double bonds can vary, leading to different isomers.
One common example is 1,4-cyclohexadiene, where the double bonds are located at carbon atoms 1 and 4. To draw this structure:
  • Start by sketching a six-membered ring, representing cyclohexane.
  • Then, add double bonds at the 1st and 4th carbon positions.
This diene is often used in various organic synthesis applications due to its reactivity.
Cyclooctatetraene
Cyclooctatetraene is a cycloalkene with the formula \(C_8H_8\). It contains an eight-membered ring with four double bonds. One common isomer is 1,3,5,7-cyclooctatetraene, where the double bonds are at positions 1, 3, 5, and 7.
Here's how to draw 1,3,5,7-cyclooctatetraene:
  • Sketch an eight-membered ring, representing cyclooctane.
  • Add double bonds at the 1st, 3rd, 5th, and 7th positions.
Cyclooctatetraene is unique because its non-aromatic structure is more stable in a non-planar tub-like conformation.
Cycloheptadiene
Cycloheptadiene is a cycloalkene with the formula \(C_7H_8\). This compound features a seven-membered ring with two double bonds. There are several possible isomers depending on the positions of the double bonds and substituents.
One example is 3-bromo-1,4-cycloheptadiene, where the double bonds are at positions 1 and 4, and a bromine atom is attached at position 3:
  • Start by drawing a seven-membered ring, representing cycloheptane.
  • Add double bonds at the 1st and 4th positions.
  • Attach a bromine atom at the 3rd position.
Another related compound is 1-bromo-1,4-cycloheptadiene, where the bromine is attached at position 1 instead of 3.
Substituted Alkenes
Substituted alkenes are alkenes (carbon-carbon double bonded compounds) that have additional atoms or groups of atoms attached, known as substituents. These substituents can significantly affect the physical and chemical properties of the molecule.
For example, in 5-methyl-1,3-cyclohexadiene:
  • The base structure is cyclohexadiene with double bonds at the 1st and 3rd positions.
  • A methyl group (–CH3) is attached at the 5th position.
Another example is 2-fluoro-1,3-cyclohexadiene:
  • It also has a cyclohexadiene base with double bonds at the 1st and 3rd positions.
  • A fluorine atom (–F) is attached at the 2nd position.
Such substitutions can affect reactivity, stability, and how the compounds participate in chemical reactions.
Drawing Chemical Structures
Drawing chemical structures is a fundamental skill in organic chemistry. To correctly depict compounds like cyclohexadiene or cyclooctatetraene, follow these steps:
  • Identify the base carbon skeleton (e.g., cyclohexane for cyclohexadienes, cyclooctane for cyclooctatetraenes).
  • Locate and draw any double bonds according to their specified positions (e.g., 1,4-positions for 1,4-cyclohexadiene).
  • Add any substituents, such as halogens or alkyl groups, at their correct positions (e.g., Br in 3-bromo-1,4-cycloheptadiene).
Always ensure your drawings clearly show the ring size, double bonds, and substituents for accurate molecule representation.

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Most popular questions from this chapter

Alkanes combine with oxygen to produce carbon dioxide and water according to the following scheme: $$ \mathrm{C}_{n} \mathrm{H}_{2 n+2}+(3 n+1) / 2 \mathrm{O}_{2} \rightarrow(n+1) \mathrm{H}_{2} \mathrm{O}+n \mathrm{CO}_{2} $$ This process is generally referred to as combustion. An important use of this reaction is the quantitative determination of elemental composition (elemental analysis). Typically, a small sample of the compound is completely burned, and the water and carbon dioxide produced are collected and weighed. From the weight of water, the amount of hydrogen in the original compound can be determined. Similarly, the amount of carbon dioxide formed allows us to determine the amount of carbon in the original compound. Oxygen, if present, is usually determined by difference. The determination of the relative molar proportions of carbon and hydrogen in a compound is the first step in deriving its molecular formula. If combustion of \(5.00 \mathrm{mg}\) of a hydrocarbon gives \(16.90\) \(\mathrm{mg}\) of carbon dioxide and \(3.46 \mathrm{mg}\) of water, what are the weight percents of carbon and hydrogen in the sample?

Draw 2-methyl-2-butene, 1-pentene, \((E)-2\)-pentene, and (Z)2-pentene. Put them in order of least stable to most stable.

Show that the \(90^{\circ}\)-rotated form of an alkene has zero overlap between the pair of carbon \(2 p_{z}\) orbitals.

Find the compound of the formula \(\mathrm{C}_{10} \mathrm{H}_{16}\) that is composed of two six-membered rings and which has only three different carbons.

Draw the following molecules: cis-2-pentene, 2-chloro-1-pentene, trans-5-iodo-2-pentene, 4-bromocyclohexene, \(1,3,6\)-cyclooctatriene.
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