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Chapter 20: Q29P (page 1038)

Rank the following carbocations in decreasing order of stability. Classify each as primary, secondary, or tertiary.

(a)

(b)

(c)

(d)

Short Answer

Expert verified

carbocations in order from most stable to least stable

Step by step solution

01

Carbocations

A species which has a carbona tom bearing only six electrons and having a positive charge is known as carbonium ion or carbocation.

02

Stability of carbocations

Greater the number of alkyl groups, greater is the dispersal of positive charge and hence greater is the stability of the carbocation.

30 carbocation with three alkyl groups is more stable than 20 carbocation with two alkyl groups which in turn are more stable than 10 carbocation with one alkyl group. However, methyl carbocation which does not contain any alkyl group is the least stable.

03

 Step 3: Carbocations in decreasing order of stability

Tertiary (30) carbocation is the most stable while the primary (10) carbocation is the least stable.

carbocations in order from most stable to least stable

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Most popular questions from this chapter

Question: Oxidation of primary alcohol to an aldehyde usually gives some over-oxidation to the carboxylic acid. Assume you have used PCC to oxidize pentan-1-ol to pentanal.

  1. Show how you would use acid-base extraction to purify the pentanal.
  2. Which of the expected impurities cannot be removed from pentanal by acid-base extractions? How would you remove this impurity?

Question:An unknown compound gives a molecular ion of m/z 70 in the mass spectrum. It reacts with semicarbazide hydrochloride to give a crystalline derivative, but it gives a negative Tollens test. The NMR and IR spectra follow. Propose a structure for this compound, and give peak assignments to account for the absorptions in the spectra. Explain why the signal at 1790 cm-1 in the IR spectrum appears at an unusual frequency.

Show how you would synthesize any of the standard amino acids from each starting material. You may use any necessary reagents.

Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.

(a) methyl salicylate

(b) methyl formate (bp 32°C)

(c) ethyl phenylacetate

Question:

  1. The Key Mechanism for Fischer esterification omitted some important resonance forms of the intermediates shown in brackets. Complete the mechanism by drawing all the resonance forms of these two intermediates.
  2. Propose a mechanism for the acid-catalyzed reaction of acetic acid with ethanol to give ethyl acetate.
  3. The Principle of Microscopic Reversibility states that a forward reaction and a reverse reaction taking place under the same conditions (as in equilibrium) must follow the same reaction pathway in microscopic detail. The reverse of the Fischer esterification is the acid-catalyzed hydrolysis of an ester. Propose a mechanism for the acid-catalyzed hydrolysis of ethyl benzoate, PhCOOCH2CH3.
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