Chapter 12: Problem 27
\(\beta\) -Ocimene, a triene found in the fragrance of cotton blossoms and several essential oils, has the IUPAC name \(c i s-3,7\) -dimethyl-1,3,6-octatriene. (Cis refers to the configuration of the double bond between carbons 3 and \(4,\) the only double bond in this molecule about which cis -trans isomerism is possible. Draw a structural formula for \(\beta\) -ocimene.
Short Answer
Step by step solution
Understand the Name
Draw the Base Chain
Add the Double Bonds
Position the Methyl Groups
Consider the Cis Configuration
Check the Structure
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
IUPAC nomenclature
- "Octatriene" indicates a chain of 8 carbon atoms (octa-) and three double bonds (-triene).
- The numbers "1, 3, 6" specify the carbon atoms where these double bonds are located.
- "Dimethyl" signifies the presence of two methyl groups (CH₃) attached to the main carbon chain.
- "3,7" clarifies the positions of these methyl groups on the carbon chain.
- "Cis" refers to the stereochemistry of the specific double bond between carbons 3 and 4.
isomerism
For \(\beta\)-ocimene, it’s crucial to understand that the position and arrangement of its double bonds and methyl groups create specific types of isomers. Among the stereoisomers, cis-trans isomerism is a notable subtype, which is highly relevant to \(\beta\)-ocimene because of its double bonds. Isomers with different spatial arrangements can behave differently in terms of reactivity and interaction with other molecules.
structural formula
- Start by drawing a chain of eight carbon atoms.
- Add double bonds between carbons 1 and 2, 3 and 4, and 6 and 7.
- Place methyl groups on carbons 3 and 7.
- Ensure that the double bond between carbons 3 and 4 has the 'cis' configuration, meaning that the additional groups on those carbons face the same direction.
cis-trans isomerism
- Cis-trans isomers generally have different boiling points and other physical properties.
- The configuration can influence the molecule’s function and interaction with other chemicals.
- In the natural world, such slight differences in spatial arrangement can significantly affect scent, flavor, and biological activity.