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Chapter 3: Q18P (page 168)

Give IUPAC names for the following cycloalkanes.

(a)

(b)

(c)

Short Answer

Expert verified

(a)cis-1-ethyl-3-methylcyclobutane

(b)trans-1-tert-butyl-3-ethyl cyclohexane

(c)trans-1,2-dimethyl cyclopropane

Step by step solution

01

Step 1:

A cycloalkane has two distinct faces. If two substituents point toward the same face, they are cis. If they point toward opposite faces, they are trans. These geometric isomers cannot interconvert without breaking and re-forming bonds.

02

(a)

Two hydrogen atoms pointed towards same face, so they are cis, ethyl group is branched at C1 and methyl group is branched at C3 position, in cyclic ring of four carbon atoms.

03

(b)

Two hydrogen atoms pointed towards opposite face, so they are trans,ethyl group is branched at C3 and tert-butyl group branched at C1 position, in cyclic ring of six carbon atoms.

04

(c)

Two hydrogen atoms pointed towards opposite face, so they are trans, two methyl groups are branched at C1 and C2 position, in cyclic ring of three carbon atoms.

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Most popular questions from this chapter

Give the IUPAC name of the following alkanes.

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)
  1. There are 18 isomeric alkanes of molecular formula C8H18. Draw and name any eight of them.
  2. Draw and name the six isomeric cyclopentane of molecular formula C7H14. These will include four constitutional isomers, of which two show geometric (cis-trans) stereoisomerism.

The following names are all incorrect or incomplete, but they represent real structures. Draw each structure and name it correctly.

(a)2-ethylpentane

(b) 3-isopropylhexane

(c) 5-chloro-4-methylhexane

(d) 2-dimethylbutane

(e) 2-cyclohexylbutane

(f)2,3-diethylcyclopentane

Construct a graph, similar to Figure 3-11, of the torsional energy of 3-methylpentanealong theC2鈭�C3.PlaceC2in front, represented by three bonds coming together in a Y shape, andC3in back, represented by a circle with three bonds pointing out from it. Define the dihedral angle as the angle between the methyl group on the front carbon and ethyl group on the back carbon. Begin your graph at 00thedihedral angle and begin to turn the front carbon. Show the Newman projection and the approximate energy at each600of rotation. Indicate which conformations are the most stable (lowest energy) and the least stable (highest energy).

Question: Write the structure for the following compounds.

(a) 3-ethyl-4-methylhexane

(b) 3-ethyl-5-isobutyl-3-methylnonane

(c) 4-tert-butyl-2-methylheptane

(d) 5-isopropyl-3,3,4-trimethyloctane
See all solutions

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