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Chapter 14: Q25P (page 737)

Question. Propose a complete mechanism for the reaction of cyclopentene oxide with sodium methoxide in methanol.

Short Answer

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Answer.

Step by step solution

01

Attack of methoxide ion as nucleophile on cyclopentene oxide:

Methoxide ion acts as a good nucleophile and attacks at the epoxide ring as epoxide is strained due to presence of angle strain and attack of nucleophile opens up epoxide ring and release strain. Methoxide ion attacks from opposite plane of epoxide as epoxide is formed above the plane, so attack of methoxide ion will be from below the plane.

Attack of methoxide ion as nucleophile

02

Formation of the product:

After ring opening of epoxide, oxygen acquires negative charge and acts as good base and abstracts proton from methanol which leads to the formation of required product and methoxide ion is formed as side product.

Formation of product

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Most popular questions from this chapter

Question. Show how you would make the following ethers, using only simple alcohols and any needed reagents as your starting materials.

(a)1-methoxypropane

(b) 2-ethoxy-2-methylbutane

(c) 4-methylbenzyl cyclopentyl ether

(d) Trans-2-ethoxycyclohexanol

(e) The TIPS ether of (d)

(f) 4-methylcyclohexyl cyclopentyl ether

Show how you would synthesize butyl isopropyl sulfide using butan-1-ol, propan-2-ol, and any solvents and reagents you need.

Show how you would use the Williamson ether synthesis to prepare the following ethers. You may use any alcohols or phenols as your organic starting materials.

  1. Cyclohexyl propyl ether
  2. Isopropyl methyl ether
  3. 1-methoxy-4-nitrobenzene
  4. Ethyl n-propyl ether (two ways)
  5. Benzyl tert-butyl ether (benzyl =Ph-CH2-)

Give a common name (when possible) and a systematic name for each compound

(a) CH3OCH=CH2

(b) CH3CH2OCH(CH3)2

(c) ClCH2CH2OCH3

(d)

e)

f)

g)

h)

i)

Show how you would accomplish the following transformations. Some of these examples require more than one step.
See all solutions

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