/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Problem 27 \(\beta\) -Ocimene, a triene fou... [FREE SOLUTION] | 91Ó°ÊÓ

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\(\beta\) -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

Expert verified
Draw an 8-carbon chain with double bonds at positions 1, 3, 6, and methyl groups at 3 and 7, ensuring cis at C3-C4.

Step by step solution

01

Understand the Name

The IUPAC name gives us several pieces of information. First, the base chain is 'octatriene,' which means there is a chain of 8 carbon atoms with three double bonds (triene). The positions of these double bonds are at carbons 1, 3, and 6. The molecule also has two methyl groups (dimethyl) at positions 3 and 7.
02

Draw the Base Chain

Start by drawing a straight chain of 8 carbon atoms for the octane backbone. Number them from 1 to 8 for clarity. Ensure that there are 8 carbon atoms in total.
03

Add the Double Bonds

Add double bonds between carbon atoms 1 and 2, 3 and 4, and 6 and 7 based on the 'octatriene' and the specific numbering provided in the name.
04

Position the Methyl Groups

Attach a methyl group (CH₃) to carbon 3 and another methyl group to carbon 7. This is indicated by '3,7-dimethyl' in the name.
05

Consider the Cis Configuration

Focus on the double bond between carbon atoms 3 and 4, where cis-trans isomerism is possible. Position the substituents around this double bond to achieve the 'cis' configuration, meaning that hydrogen atoms or methyl groups on these carbons should be on the same side of the double bond.
06

Check the Structure

Verify that all parts of the molecule match the IUPAC name: a chain of 8 carbons, three double bonds at specified positions, methyl groups at carbons 3 and 7, and ensure that the double bond between carbons 3 and 4 possesses the 'cis' configuration.

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Key Concepts

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

IUPAC nomenclature
IUPAC nomenclature is a systematic method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It ensures that every compound has a unique and unambiguous name. In the case of \(\beta\)-ocimene, its IUPAC name is \(cis-3,7\)-dimethyl-1,3,6-octatriene. Here’s what each part of the name tells us:
  • "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.
This systematic approach allows chemists around the world to understand exactly which molecule is being referenced just by looking at its name.
isomerism
Isomerism describes the phenomenon where two or more compounds have the same molecular formula but different structures or arrangements of atoms. This can lead to compounds having distinct physical and chemical properties. It includes several types: structural isomerism and stereoisomerism. In structural isomerism, the atoms are connected in different ways, leading to different functional groups or positions within the molecule. Meanwhile, stereoisomerism involves the same connectivity of atoms, but with different spatial orientations.
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
The structural formula of a compound graphically represents its molecular arrangement. It displays how atoms are bonded within the molecule, including the arrangement and connectivity of carbon atoms, the placement of functional groups, and more. This is vital for understanding how a molecule might interact in chemical reactions.For \(\beta\)-ocimene, the structural formula provides a visual of its 8-carbon backbone with the precise placement of double bonds and methyl groups. Here’s how to draw it:
  • 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.
The completed structure helps chemists visualize how \(\beta\)-ocimene might react with other substances and the different conditions affecting its reactivity.
cis-trans isomerism
Cis-trans isomerism is a type of stereoisomerism specifically related to the positioning of substituents around a double bond or a particular structure in a molecule. In these isomers, the connectivity of the atoms remains the same, but the three-dimensional arrangement differs. This can lead to significant differences in the physical and chemical properties of the isomers.For instance, the term "cis" indicates that two substituents are on the same side of the double bond, whereas "trans" would mean they are on opposite sides. In the case of \(\beta\)-ocimene, the designation 'cis' in the name \(cis-3,7\)-dimethyl-1,3,6-octatriene highlights that the substituents (methyl groups and hydrogens in this case) on carbons 3 and 4 are positioned on the same side of the molecule's double bond.
  • 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.
Understanding cis-trans isomerism is crucial in organic chemistry, especially for molecules involved in biological processes or material sciences.

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Most popular questions from this chapter

Propose an explanation for the following experimental observations: 1\. Acid-catalyzed hydration of 1-hexene gives a single alcohol in high yield. 2\. Acid-catalyzed hydration of cis- or trans-2-hexene gives a mixture of two alcohols in approximately equal amounts. 3\. Acid-catalyzed hydration of \(c i s\) - or trans-3-hexene gives a single alcohol in high yield.

Answer true or false. (a) A phenyl group has the molecular formula \(\mathrm{C}_{6} \mathrm{H}_{5}-\) and is represented by the symbol \(\mathrm{Ph}-\) (b) Para substituents occupy adjacent carbons on a benzene ring. (c) 4 -Bromobenzoic acid can be separated into cis and trans isomers.

Answer true or false. (a) Alkenes and alkynes are nonpolar molecules. (b) The physical properties of alkenes are similar to those of alkanes of the same carbon skeletons. (c) Alkenes that are liquid at room temperature are insoluble in water and when added to water, will float on water.

Answer true or false. (a) Phenols and alcohols have in common the presence of an \(-\) OH group. (b) Phenols are weak acids and react with strong bases to give water-soluble salts. (c) The \(\mathrm{p} K_{\mathrm{a}}\) of phenol is smaller than that of acetic acid.

Answer true or false. (a) Benzene does not undergo the addition reactions that are characteristic of alkenes. (b) A defining feature of aromatic compounds is that they are highly unsaturated but do not undergo characteristic alkene addition reactions. (c) Nitration of benzene adds a \(-\mathrm{NO}_{2}\) group to one of the carbons of the aromatic ring. (d) Halogenation of an alkene is an addition reaction; halogenation of an arene is a substitution reaction.

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