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Chapter 7: PROBLEM7.37 (page 286)

Question: Rank the following carbocations in order of increasing stability.

a.

b.

c.

Short Answer

Expert verified

ANSWER

The order of increasing stability is :a<b<c

Step by step solution

01

Carbocations

Carbocations are the ionic species that contain a positive charge on the carbon atom.

02

Stability of carbocations

The factors affecting the stability of the carbocations are as follows:

  • Multiple bonds: A double or a triple bond adjacent to the carbocations impart exceptional stability to the carbocation.
  • Hyperconjugation: The stability order of the carbocation increases in the manner CH3+1°<2°<3
  • Lone pairs on adjacent carbon atom to the carbocationic center provide stability to the carbocation.
03

Determination of the order of increasing stability

a. Vinyl carbocations are very less stable, even less than the primary carbocations. Hence, (a) is least stable among the given carbocations.

b. The given compound is a secondary carbocation. Hence, it is the most stable among the given compounds.

c. Given is the primary carbocation. It has intermediate stability (more than the vinyl carbocations).

Hence, the order of increasing stability is a<b<c.

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Most popular questions from this chapter

Question: Draw the eight constitutional isomers having the molecular formula C5H11Cl .

  1. Give the IUPAC name for each compound (ignoring R and S designations).
  2. Classify each alkyl halide as 1°,2°or3°.
  3. Label any stereogenic centers.
  4. For each constitutional isomer that contains a stereogenic center, draw all possible stereoisomers, and label each stereogenic center as R or S.

Question: Determine the mechanism and draw the products of each reaction. Include the stereochemistry at all stereogenic centers.

a.

b.

c.

d.

Question: Identify the stronger nucleophile in each pair of anions.

a. Br- or Cl- in a polar protic solvent.

b. OH-or Cl- in a polar aprotic solvent.

c. HS- or F- in a polar protic solvent.

Question: For each alkyl halide and nucleophile:

[1] Draw the product of nucleophilic substitution.

[2] determine the likely mechanism (or) for each reaction.

a.

b.

c.

d.

Question: Pick the reactant or solvent in each part that gives the faster SN2 reaction.

  1. reaction of with OH- or CH3CH2Br
  2. reaction of CH3CH2CH2Cl NaOH or NaOCOCH3
  3. reaction of CH3CH2CH2I with -OCH3 in or DMSO
See all solutions

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