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Chapter 7: Q12P-a (page 197)

Rank the substituents in each of the following sets according to the sequence rules:

-CH3,-OH,-H,-Cl

Short Answer

Expert verified

Higher to lower-ranking:-Cl>-OH>-CH3>-H

Step by step solution

01

E and Z designation

This naming scheme only applies to substituted alkenes that have two substituents other than hydrogen on the double bond. But when trisubstituted and tetrasubstituted of the double bond are present then the E and Z system is used for describing alkene stereochemistry.

02

Rule for ranking substituents

  • Consider each of the double-bond carbons separately and ranks the two substituents according to the atomic number of the first atom in each. An atom with a higher atomic number will rank higher.
  • If the first atom same then, look at the second, third, or fourth atoms away from the double-bond until the first difference is found.
  • Multiple-bonded atoms are equivalent to the same number of single-bonded atoms.
03

Ranking of given groups

As ranking is atomic number dependent, more the atomic number higher will be ranking. So,

  • Chlorine ranks higher than oxygen.
  • Oxygen ranks higher than carbon.
  • Carbon ranks higher than hydrogen.
  • Higher to lower ranking:-Cl>-OH>-CH3>-H

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Most popular questions from this chapter

What about the second step in the electrophilic addition of HCl to an alkene—the reaction of chloride ion with the carbocation intermediate? Is this step exergonic or endergonic? Does the transition state for this second step resemble the reactant (carbocation) or product (alkyl chloride)? Make a rough drawing of what the transition-state structure might look like.

Rank the carbocations below in terms of increasing stability:

Question: Loratadine, marketed as an antiallergy medication under the name Claritin, has four rings, eight double bonds, and the formula C22H?CIN2O2 . How many hydrogens does loratadine have? (Calculate your answer; don’t count hydrogens in the structure.)

Sketch the transition-state structures involved in the reaction of HBr with 1-pentene (Problem 7-69). Tell whether each structure resembles reactant or product.

Draw an energy diagram for the addition of HBr to 1-pentene. Let one curve on your diagram show the formation of 1-bromopentane product and another curve on the same diagram show the formation of 2-bromopentane product. Label the positions for all reactants, intermediates, and products. Which curve has the higher-energy carbocation intermediate? Which curve has the higher-energy first transition state?
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