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Chapter 5: Problem 19

\(\beta\)-Ocimene, a triene found in the fragrance of cotton blossoms and several essential oils, has the IUPAC name (Z)-3,7-dimethyl- \(1,3,6\)-octatriene. Draw a structural formula for \(\beta\)-ocimene.

Short Answer

Expert verified
Answer: The structural formula for β-ocimene is: CH2=C(CH3)-C(H)=C(H)(Z)-CH=C(CH3)-CH=CH2

Step by step solution

01

Draw the carbon skeleton

Draw a straight chain of 8 carbons extending horizontally. This represents the main chain of the molecule.
02

Add double bonds

Add double bonds between carbons 1 and 2, 3 and 4, and 6 and 7. This is based on the octatriene portion of the IUPAC name, which indicates that there are double bonds at positions 1, 3, and 6.
03

Add the (Z)-configuration

For the double bond between carbons 3 and 4, draw the (Z)-configuration. This means that the two highest-priority groups are on the same side of the double bond. In this case, the higher-priority groups on carbon 3 and carbon 4 are the two hydrogens. Draw the hydrogens on the same side of the double bond (either on top or bottom).
04

Add methyl groups

Add methyl groups (-CH3) to carbons 3 and 7, as indicated by the 3,7-dimethyl part of the IUPAC name.
05

Complete the structure

Add hydrogens to each carbon, ensuring each carbon has a total of 4 bonds (remembering that each double bond counts as 2 bonding sites). As a final check, make sure that the molecule has a total of 8 carbons, with double bonds at positions 1, 3, and 6, the (Z)-configuration for the 3-4 double bond, and methyl groups at positions 3 and 7. The resulting structure represents the molecule of β-ocimene.

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Most popular questions from this chapter

Draw structural formulas for these alkenes. (a) trans-2-Methyl-3-hexene (b) 2-Methyl-2-hexene (c) 2-Methyl-1-butene (d) S-Ethyl-3-methyl-1-pentene (e) 2,3-Dimethyl-2-butene (f) cis-2-Pentene (g) (Z)-1-Chloropropene (h) S-Methylcyclohexene (i) 1-Isopropyl-4-methylcyclohexene (j) (E)-2,6-Dimethyl-2,6-octadiene (k) 3-Cyclopropyl-1-propene (1) Cyclopropylethene (m) 2-Chloropropene (n) Tetrachloroethylene (o) 1-Chlorocyclohexene

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Name and draw structural formulas for all alkenes with the molecular formula \(\mathrm{C}_{5} \mathrm{H}_{10}\). As you draw these alkenes, remember that cis and trans isomers are different compounds and must be counted separately.
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