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Chapter 14: Q 45P (page 748)

Show how you would synthesize the following ethers in good yields from the indicated starting materials and any additional reagents needed.

(a) Cyclopentyl n propyl etherfromcyclopentanolandpropan-1-ol.

(b) n-butyl phenyl etherfromphenolandbutan-1-ol.

(c) 2-ethoxyoctanefrom anoctene

(d) 1-methoxydecanefrom adecene

(e) 1-ethoxy-1-methylcyclohexanefrom 2-methylcyclohexanol.

(f) trans-2,3-epoxyoctane from octane-2-ol.

Short Answer

Expert verified

a)

b)

c)

d)

e)

f)

Step by step solution

01

Ethers

The functional group is which two alkyl groups are bonded to an oxygen atom are known as ethers. Ethers have the general formula R-O-R', where R and R' represent alkyl groups.

02

Synthesis of ethers

(a)

synthesis of cyclopentyl n-propyl ether fromcyclopentanol and propan-2-ol.

(b)


synthesis of n-butyl phenyl ether from phenol and butan-1-ol.

(c)

Synthesis of 2-ethoxyoctane from octene.

(d)

Synthesis of 1-methyldecane from decene.

(e)

Synthesis of 1-ethoxy-1-methylcyclohexane from 2- methylcyclohexanol.

(f)

Synthesis of trans-2,3-epoxyocrane from octan-2-ol.

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Most popular questions from this chapter

Write structural formulas for the following compounds

  1. methyl isopropyl ether (b) di-iso-butyl ether (c) 2-methoxyoctane

(d) diallyl ether (e) allyl ethyl ether (f) cycloheptane oxide

(g) trans-2,3-epoxyheptane (h) (2R,3S)-2-ethoxypentan-3-ol (i) cis-2,3-dimethyloxirane

Propylene oxide is a chiral molecule. Hydrolysis of propylene oxide gives propylene glycol, another chiral molecule.

(a) Draw the enantiomers of propylene oxide.

(b) Propose a mechanism for the acid-catalyzed hydrolysis of pure (R)-propyleneoxide.

(c) Propose a mechanism for the base-catalyzed hydrolysis of pure (R)-propyleneoxide.

(d) Explain why the acid-catalyzed hydrolysis of optically active propylene oxide gives a product with lower enantiomeric excess and a rotation opposite that of the product of the base- catalyzed hydrolysis.

Aluminum trichloride () dissolves in ether with the evolution of a largeamount of heat. (In fact, this reaction can become rather violent if it gets too warm.)Show the structure of the resulting aluminum chloride etherate complex.

Question. Glycerol (propane-1,2,3-triol) is a viscous syrup with molecular weight 92g/mol, boiling point 290oC, and density 1.24g/mol. Transforming the three hydroxy groups into their trimethylsilyl ethers (using chlorotrimethylsilane and a tertiary amine) produces a liquid that flows easily, has molecular weight 309g/mol, boiling point approximately 180oC, and density 0.88g/mol. Draw the structures of these two compounds and explain why glycerol has a lower molecular weight but a much higher boiling point and density.

Predict the major product when each reagent reacts with ethylene oxide.

(a) NaOCH2CH3(Sodium ethoxide)

(b) NaNH2(sodium amide)

(c) NaSPh (sodium thiophenoxide)

(d) PhNH2(aniline)

(e) KCN (potassium cyanide)

(f) NaN3(soidum azide)
See all solutions

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