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Chapter 7: Q12P-c (page 197)

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

-CO2H,-CH2OH,-C鈮�N,-CH2NH2

Short Answer

Expert verified

Higher to lower-ranking:

Step by step solution

01

E and Z designation

Only disubstituted alkenes with two substituents other than hydrogen on the double bond can use the cis-trans system of naming. But when trisubstituted and tetrasubstituted of the double bond is 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,

  • In-CO2H carbon is attached to three oxygen.
  • In-CH2OH carbon is attached to two hydrogens and one oxygen.
  • In -C鈮�Ncarbon is attached to three nitrogen.
  • In -CH2NH2carbon is attached to two hydrogens and one nitrogen.

So, higher to lower-ranking:-CO2H>-CH2OH>-C鈮�N>-CH2NH2

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Most popular questions from this chapter

Question. Draw and name the six alkene isomers, C5H10 , including E, Zisomers:

Name the following alkenes:

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?

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

-CH3,-OH,-H,-Cl

What about the second step in the electrophilic addition of HCl to an alkene鈥攖he 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.
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