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Chapter 20: Q30P (page 1038)

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

(a)

(b)

(c)

(d)

Short Answer

Expert verified

radicals in order from most stable to least stable

Step by step solution

01

Free radicals

An atom or group of atoms containing odd or unpaired electron is known as the free radical. The unpaired electron is represented by a single unpaired dot in the formula. Free radicals are electrically neutral. They are highly reactive species formed by homolytic fission of a covalent bond.

02

Stability of free radicals

Tertiary alkyl radical is more stable than secondary alkyl radical which in turn is more stable than primary alkyl radical. However, methyl free radical which does not contain any alkyl group is the least stable.

03

Free radicals in decreasing order of stability

Tertiary allylic radical is the most stable than tertiary since it is stabilized by resonance while the primary radical is the least stable.

radicals in order from most stable to least stable

Resonance delocalization is particularly effective in stabilizing a radical.

tertiary allylic radical stabilized by resonance

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Most popular questions from this chapter

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(a)trans-1-产谤辞尘辞产耻迟-2-别苍别鈫�trans-pent-3-enoic acid (two ways)

(b)hex-3-ene鈫抪ropanoic acid

(c) but-2-enal鈫抌ut-2-enoic acid

(d) hexanoic acid鈫抙exanal

(e)

(f)

(g)

(h)

Phenols (pKa鈮� 10) are more acidic than other alcohols, so they are easily deprotonated by sodium hydroxide or potassium hydroxide. The anions of phenols (phenoxide ions) can be used in the Williamson ether synthesis, especially with very reactive alkylating reagents such as dimethyl sulfate. Using phenol, dimethyl sulfate, and other necessary reagents, show how you would synthesize methyl phenyl ether.

Question: Arrange each group of compounds in order of increasing basicity.

  1. CH3COO-,CICH2C00- , and PhO-
  2. sodium acetylide, sodium amide, and sodium acetate
  3. sodium benzoate, sodium ethoxide, and sodium phenoxide
  4. pyridine, sodium ethoxide, and sodium acetate

(a) Give the products expected when acetic formic anhydride reacts with

(i) aniline and

(ii) benzyl alcohol

(b) Propose mechanisms for these reactions.

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.
See all solutions

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