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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: As you will learn in Chapter 9, the epoxide is an ether with an oxygen atom in a three-membered ring. Epoxides can be made by intramolecular SN2 reactions of intermediates that contain a nucleophile and a leaving group on adjacent carbons, as shown.

Assume that each of the following starting materials can be converted to an epoxide by this reaction. Draw the product formed (including stereochemistry) from each starting material. Why might some of these reactions be more difficult than others in yielding nucleophilic substitution products?

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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: Device a synthesis of each compound from an alkyl halide using any other organic or inorganic reagents.

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Question: Explain why quinuclidine is a much more reactive nucleophile than triethylamine, even though both compounds have N atoms surrounded by three R groups.

Question: Classify each solvent as protic or aprotic.

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  2. CH3NO2
  3. CH2Cl2
  4. NH3
  5. N(CH3)3
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See all solutions

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