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Chapter 14: Q28P (page 741)

Give the expected products of the following reactions. Include a protonation step where necessary.

  1. 1,2-dimethyloxirane + isopropylmagnesium bromide
  2. ethyl oxide + n-butyllithium
  3. cyclohexyloxirane + ethyllithium

Short Answer

Expert verified

Answer

(c)

Step by step solution

01

isopropyl magnesium bromide

We can use Grignard reagents to convert epoxide to alcohol. At first the epoxide is converted bto organo magnesium bromide compound. And then it will converted to alcohol by the addition of base or water.

02

n- Butyllithium

As Grignard reagent it will convert the epoxide to alcohol. At first it will convert it to organo lithium compound and then it will convert to alcohol.

03

Ethyllithium

This is used to convert the epoxide to organolithium and to alcohol. But here is a possibility to give one minor product when the organo lithium compound is attack to the carbon which is attached to the cyclohexane. This will be the less stable product in this

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Most popular questions from this chapter

Question. The following reaction resembles the acid-catalyzed cyclization of squalene oxide. Propose a mechanism for this reaction.

One of the crowning achievements of natural products synthesis was Bryostatin 1, published by Professor Gary Keck (University of Utah; Journal of the American Chemical Society,2011, 133, 744-747). The Bryostatins are a family of compounds isolated from aquatic invertebrates known as Bryozoans. The compounds are of interest for a variety of biological effects, including anti-cancer activity and reversing brain damage in rodents.

a. How many ether functional groups are present in Bryostatin 1?

b. Identify the other oxygen-containing functional groups.

c. This is called a macrolide because it contains a large number of atoms in the large ring. How many atoms are in the large ring?

d. How many chiral centers are in this molecule?

e. Using the number of chiral centers you reported in part (d), calculate the number of stereoisomers possible at these chiral centers. (Ignore stereoisomers at double bonds.)

Show how the following ethers might be synthesized using (1) alkoxymercuration-demercuration and (2) the Williamson synthesis. (When one of these methods cannot be used for the given ether, point out why it will not work.)

  1. 2-methoxybutane
  2. Ethyl cyclohexyl ether
  3. 1-methoxy-2-methylcyclopentane
  4. 1-methoxy-1-methylcyclopentane
  5. 1-isopropoxy-1-methylcyclopentane
  6. Tert-butyl phenyl ether

Question: Both LiAlH4and Grignard reagents react with carbonyl compounds to give alkoxide ion intermediates (that become protonated in an aqueous workup). Those alkoxides can react with 1o or methyl alkyl halides or tosylates to give ethers. Show how the following ethers can be formed in this two -step process. As starting materials, you may use any reactants containing 8carbons or fewer.

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
See all solutions

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