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Chapter 21: 27P (page 817)

Which compound in each pair forms the higher percentage of gem-diol at equilibrium?

a.

or

b.

or

Short Answer

Expert verified

a.

b.

Step by step solution

01

Hydrate formation

Carbonyl compounds would undergo hydration to form diols. The thermodynamic stability of the hydrate would depend on the nature of substituents on the carbonyl carbon.

02

 Comparison of given compounds  

Consider the given pair of organic compounds,

a. Among the given compounds, butanal would form the higher percentage of gem-diols at equilibrium than but-2-one.

This occurs because alkyl group being electron-releasing group (ERG) would stabilize the carbonyl compound shifting the equilibrium backward.

Given pair a.

b. Among the given compounds, 2,2-difluropropanal would form the higher percentage of gem-diols at equilibrium than propan-1-al.

This occurs because halides being an electron-withdrawing group (EWG) would destabilize the carbonyl compound shifting the equilibrium forward.

The presence of fluoride ions would develop a partial positive charge on the alpha-carbon, which would destabilize the carbonyl carbon.

Given pair b.

03

Stable carbonyl compound

The carbonyl compound that would give a higher percentage of gem-diol is as follows:

a.

Compound that forms the higher percentage of gem-diol at equilibrium in pair a.

Compound that forms the higher percentage of gem-diol at equilibrium in pair b.

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Most popular questions from this chapter

A solution of acetone (CH3)2C=O in ethanol CH3CH2OH in the presence of a trace of acid was allowed to stand for several days, and a new compound of molecular formula C7H16O2 was formed. The IR spectrum showed only one major peak in the functional group region around 3000 cm-1 , and the 1H-NMR spectrum is given here. What is the structure of the product?

Besides the tert-butyldimethylsilyl ethers introduced in Chapter 20, there are many other widely used alcohol protecting groups. For example, an alcohol such as cyclohexanol can be converted to a methoxy methyl ether (a MOM protecting group) by treatment with base and chloromethyl methyl ether, . The protecting group can be removed by treatment with aqueous acid.

a. Write a stepwise mechanism for the formation of a MOM ether from cyclohexanol.

b. What functional group comprises a MOM ether?

c. Besides cyclohexanol, what other products are formed by aqueous hydrolysis of the MOM ether? Draw a stepwise mechanism that accounts for formation of each product.

Rank the following compounds in order of increasing reactivity towards nucleophilic attack.

An unknown compound D exhibits a strong absorption in its IR spectrum at 1692 cm-1 . The mass spectrum of D shows a molecular ion at m/z = 150 and a base peak at 121. The 1H- NMR spectrum of D is shown below. What is the structure of D?

Maltose is a carbohydrate present in malt, the liquid obtained from barley and other grains. Although maltose has numerous functional groups, its reactions are explained by the same principles we have already encountered.

a. Label the acetal and hemiacetal carbons.b. What products are formed when maltose is treated with each of the following reagents: [1] ; [2] and HCl; [3] excess NaH, then excess ?c. Draw the products formed when the compound formed in Reaction [3] of part (b) is treated with aqueous acid.The reactions in parts (b) and (c) are used to determine structural features of carbohydrates like maltose. We will learn much more about maltose and similar carbohydrates in Chapter 28.
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