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Chapter 4: Q.62. (page 128)

Question: Draw the three constitutional isomers having molecular formula C7H14that contain a five-membered ring and two methyl groups as substituents. For each constitutional isomer that can have cis and trans isomers, draw the two stereoisomers.

Short Answer

Expert verified

Answer

Constitutional isomers

Cis and Trans isomers

Step by step solution

01

Molecular formula

The molecular formula of a compound describes the number of atoms of each kind of element present.

One or more compounds with different structures can have the same molecular formula.

02

Constitutional isomerism

Compounds with the same molecular formula may differ in terms of connectivities and bonding between their atoms.

Such varied connectivities for the same molecular formula give rise to constitutional isomers for the given molecular formula.

03

Draw the constitutional isomers for the given molecular formula

Draw a five-membered ring and two methyl groups in each of the three isomeric structures. To make three isomeric structures, the relative positions of the two methyl groups on all three five-membered rings must be different.

Hence, the three isomeric structures are:

Constitutional isomers

Out of the three constitutional isomers, the second and third structures, i.e., 1,2-dimethylcyclopentane and 1,3-dimethylcyclopentane, can have cis and trans isomers. Hence, the two cis and trans isomers are:

Cis and trans isomers

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Most popular questions from this chapter

Question: Mineral oil, a mixture of high molecular weight alkanes, is sometimes used as a laxative. Why are individuals who use mineral oil for this purpose advised to avoid taking it at the same time they consume foods rich in fat-soluble vitamins such as vitamin A?

Question: Hydrocarbons like benzene are metabolized in the body to arene oxides, which rearrange to form phenols. This is an example of a general process in the body, in which an unwanted compound (benzene) is converted to a more water-soluble derivative called a metabolite, so that it can be excreted more readily from the body.

a. Classify each of these reactions as oxidation, reduction, or neither.

b. Explain why phenol is more water soluble than benzene. This means that phenol dissolves in urine, which is largely water, to a greater extent than benzene.

Question: a. Using Newman projections, draw all staggered and eclipsed conformations that result from rotation around the bond highlighted in pink in each molecule;

b. draw a graph of energy versus dihedral angle for rotation around this bond.

Question: Give the structure corresponding to each IUPAC name.

  1. 3-methylhexane
  2. 3,3-dimethylpentane
  3. 3,5,5-trimethyloctane
  4. 3-ethyl-4-methylhexane
  5. 3-ethyl-5-isobutylnonane

Question: When two six-membered rings share a C-C bond, this bicyclic system is called decalin. There are two possible arrangements: trans-decalin having two hydrogen atoms at the ring fusion on opposite sides of the rings, and cis-decalin having the two hydrogens at the ring fusion on the same side.

  1. Draw trans- and cis-decalin using the chair form for the cyclohexane rings.
  2. The trans isomer is more stable. Explain why.
See all solutions

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