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Chapter 14: Q29P (page 746)

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

Short Answer

Expert verified

Answer

(e)

Step by step solution

01

methyl isopropyl ether

IUPAC name of this compound is methyl isopropyl ether. In this structure isopropyl group is with methyl ether.

02

di-iso-butyl ether

This compound is di-iso-butyl ether. There are two isobutyl groups with ether

03

2-methoxyoctane

The name of this compound is 2-methoxyoctane. Octane is present with 2 position of methoxy group.

(c)

04

di allyl ether

This is di allyl ether. Two allyl groups is present with ether middle

05

Allyl ethyl ether

This allyl ethyl ether. Allyl and ether groups are with ether.

(e)

06

Cycloheptene oxide 

The nasme of this cyclic compound is cycloheptene. Epoxide is with cycloheptane.

07

Trans-2,3-epoxyhexane 

This is trans 2,3- epoxyhexane. As 2, 3 position the epoxy group is present as trans position in this compound.

08

(2R,3S)-2-ethoxypentane-3-ol

This structure contains stereochemistry with R S configuration. This is with pentane 3 position OH and 2R, 3S configuration. The name of this compound is (2R,3S) -2-ethoxypentane.

09

Cis-2,3-dimethyloxirane

This is cis-2,3-dimethyloxirane. Two methyls are in cis position in epoxide

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Most popular questions from this chapter

Rank the given solvents in decreasing order of their ability to dissolve each compound

(a) HCOO-Na+

(b)

(c)


Solvents

Ethyl ether, water, ethanol, dichloromethane

(Another true story) An organic lab student carried out the reaction of methyl magnesium iodide with acetone (CH3COCH3), followed by hydrolysis. During the distillation to isolate the product, she forgot to mark the vials she used to collect the fractions. She turned in a product of formula C4H10Othat boiled at 350C.The IR spectrum showed only a weak O-Hstretch around 3300 cm-1, and the mass spectrum showed a base peak at m/z 59.The NMR spectrum showed a quartet (J = 7Hz) of area 3at 未1.3Propose a structure for this product, explain how it corresponds to the observed spectra, and suggest how the student isolated this compound.

There are two ways of making 2-ethoxyoctane from octan-2-ol using the Williamson ether synthesis. When pure (-) -octan-2-ol of specific rotation -8.240is treated with sodium metal and then ethyl iodide, the product is 2-ethoxyoctane with a specific rotation of -15.60. When pure (-) -octan-2-ol is treated with tosyl chloride and pyridine and then with sodium ethoxide, the product is also 2-ethoxyoctane. Predict the rotation of the 2-ethoxyoctane made using the tosylation/sodium ethoxide procedure, and propose a detailed mechanism to support your prediction.

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.
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