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Chapter 10: Q48P (page 538)

Grignard reagents react slowly with oxetane to produce primary alcohols. Propose a mechanism for this reaction, and suggest why oxetane reacts with Grignard reagents even though most ethers do not.

Short Answer

Expert verified

When Grignard reagent reacts with oxetane, it produces primary alcohol very slowly. There is a cleavage of bonds in the oxetane ring by the Grignard reagent.A new C-C bond is formed.

Step by step solution

01

Grignard reaction with oxetane

When Grignard reagent reacts with oxetane, it produces primary alcohol very slowly. There is a cleavage of bonds in the oxetane ring by the Grignard reagent.A new C-C bond is formed.

02

 Step 2: Mechanism of oxetane with Grignard reagent

The mechanism of the Grignard reagent with oxetane is similar to epoxide cleavage in ethylene oxide by the Grignard reagent. In this, the driving force is the presence of 4-membered cyclic ether, which relieves ring strain. That is why it undergoes a Grignard reaction while most other ethers do not

.

Mechanism of oxetane with Grignard reagent

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Most popular questions from this chapter

Question: Show two ways you could synthesize each of the following secondary alcohols by adding an appropriate Grignard reagent to an aldehyde.

a.

b.

c.

Give IUPAC names for the following compounds.

a.

b.

c.

A nitro group (-NO2) effectively stabilizes a negative charge on an adjacent carbon atom through resonance:

Two of the following nitrophenols are much more acidic than phenol itself. The third compound is only slightly more acidic than phenol. Use resonance structures of the appropriate phenoxide ions to show why two of these anions should be unusually stable.

Compare the properties of propan-2-ol (I) and the hexafluoro analog II

(I) mol. wt. 60 g/mole boiling point 82 °C

dipole moment 1.66 D

pKa16.5

(II)mol. wt. 168 g/mole boiling point 58 °C

dipole moment 0.32 D

pKa9.3

(a) Compound II has almost triple the molecular weight of I, but II has a lower boiling point. Explain.

(b) Explain why the dipole moment of Compound II is much lower than the dipole moment of I, despite the presence of the six electronegative fluorine atoms.

(c) Why is II a stronger acid than I?

Draw the structures of the following compounds. (Includes both new and old names.)

(a) diphenylmethanol

(b) 3-(chloromethyl)heptan-3-ol

(c) 3-cyclohexen-1-ol

(d) 3-cyclopentylhexan-2-ol

(e) meso-3,5-heptanediol

(f) cyclohexene glycol

(g) 3-(bromomethyl)phenol

(h) (2R,3R)-2,3-pentanediol

(i) cyclohex-3-ene-1-thiol

(j) diethyl disulfide

(k) 2-methylhex-4-yn-2-ol
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