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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

Propose a fragmentation to account for each numbered peak in the mass spectrum of n-butyl isopropyl ether.

Mustard gas, Cl-CH2CH2-CH2CH2-Cl, was used as a poisonous chemical agent in World War I. Mustard gas is much more toxic than a typical primary alkyl chloride. Its toxicity stems from its ability to alkylate amino groups on important metabolic enzymes, rendering the enzymes inactive.

  1. Propose a mechanism to explain why mustard gas is an exceptionally potent alkylating agent.
  2. Bleach (sodium hypochlorite,NaOCl, a strong oxidizing agent) neutralizes and inactivates mustard gas. Bleach is also effective on organic stains because it oxidizes colored compounds to colorless compounds. Propose products that might be formed by the reaction of mustard gas with bleach.

(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 δ1.3Propose a structure for this product, explain how it corresponds to the observed spectra, and suggest how the student isolated this compound.

Question. The 2001 Nobel Prize in Chemistry was awarded to three organic chemists who have developed methods for catalytic asymmetric synthesis. An asymmetric (or enantioselective) synthesis is one that converts an achiral starting material into mostly one enantiomer of a chiral product. K. Barry Sharpless (The Scripps Research Institute) developed an asymmetric epoxidation of allylic alcohols that gives excellent chemical yields and greater than 90% enantiomeric excess.

The Sharpless epoxidation uses tert-butyl hydroperoxide, titanium(IV) isopropoxide, and a dialkyl tartarate ester as the reagents. The following epoxidation of geraniol is typical.

  1. Which of these reagents is most likely to be the actual oxidizing agent? That is, which reagent is reduced in the reaction? What is the likely function of the other reagents?
  2. When achiral reagents react to give a chiral product, that product is normally formed as a racemic mixture of enantiomers. How can the Sharpless epoxidation give just one nearly pure enantiomer of the product?
  3. Draw the other enantiomer of the product. What reagents would you use if you wanted to epoxidize geraniol to give this other enantiomer?

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.

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