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Chapter 10: Q12P (page 513)

Question: Predict the products of the following reactions.

(a)CH3CH2Br+Mg鈫�ether

(b) isobutyliodide+2Li鈫�hexane

(c) 1-bromo-4-fluorocyclohexane+Mg鈫�THF

(d) CH2=CCl-CH2CH3+2Li鈫�ether

Short Answer

Expert verified

Answer

(a) CH3CH2MgBr

(b)

(c)

(d)

(e)

Step by step solution

01

Organic reactions

Organic reactions involve the reagents like Grignard reagent (R-Mg-X) and organolithium reagents (R-Li). This reaction occurs in a solvent like dry ether, THF, and hexane.

02

Products of the reactions (a) and (b)

a. When bromoethane reacts with Mg in the presence of dry ether, it results in the formation of Grignard reagent (R-Mg-X).

CH3CH2Br+Mg鈫�etherCH3CH2MgBr

b. When R-X reacts with Li in the presence of hexane, it results in the formation of alkyllithium reagent and LiX.


Formation of product

03

 Step 2: Products of the reactions (c) and (d)

d. When 1-bromo-4-fluorocyclohexane reacts with Mg in the presence of THF, it forms Grignard reagent (R-Mg-X).


Formation of product

e. When 2-chlorobutene reacts with Li (2 Equiv.) in the presence of ether, it forms organolithium reagent and LiCl.


Formation of product

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Most popular questions from this chapter

Grignard reagents react slowly with oxetane to produce primary alcohols. Propose a mechanism for this reaction, and suggest why oxetane reacts with Grignard reagents even though most ethers do not.

Ever since the Grignard reaction was discovered to react with ethylene oxide, chemists have experimented with other epoxides to test the limits of this reaction (which chemists call the scope of the reaction). The conclusion is that the success of the Grignard reaction is limited by the steric hindrance in the epoxide. One group published results of several Grignard reagents on one epoxide; one of their products is shown here. What Grignard reagent and what epoxide were used to make this compound? Comment on the steric requirements of the epoxide and the stereochemistry of the product.

Give systematic (IUPAC) names for the following diols and phenols.

For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.

Show how you would synthesize each tertiary alcohol by adding an appropriate Grignard reagent to a ketone.

(a)3-phenylhexane-3-ol (3ways)

(b) Ph3 COH

(c) 1-ethylcyclopentanol

(d) 2-cyclopentylpentan-2-ol
See all solutions

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