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Magazine Chapter 3: Q52 (page 190)
Question: This is a Newman projection of a substituted cyclohexane.
(a) Draw the equivalent chair form
(b)Draw the equivalent structure using wedge and dash notation on a cyclohexane hexagon.
(c) Give the IUPAC name.
Short Answer
Answer
a.
b.
c. IUPAC name is trans -1-chloro-3 ethylcyclohexane
Step by step solution
IUPAC nomenclature
A systematic way of naming organic compounds based on their chemical composition and structure is given by IUPAC nomenclature.
Newman projection
Newman projections are often used in drawing conformations. In Newman鈥檚 projection, one views the bond end on along the axis of connection. The front carbon is represented by the intersection of bonds, while the rear carbon appears as a circle.
Drawing cis and trans isomers for cycloalkanes
In the case of cycloalkanes, if the two substituents point toward the same faces, they are known as cis-isomers. Again, if the two substituents point toward the opposite faces, they are known as trans-isomers. These two geometric isomers cannot interconvert without breaking and forming the bonds again.
Structure and IUPAC name
a.
b.
c.
Chlorine atom is at carbon-1 while an ethyl group is at carbon-3. These two groups are trans to each other.
Hence, the IUPAC name will be trans -1-chloro-3 ethylcyclohexane
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