Problem: Select the keyword or phrase that will best complete each sentence. Key terms:addition        a base removes        weaker        enol        keto        thermodynamic        stronger        an acid adds        acyl substitution        kineticThe tautomer _______ has a C=O and an additional C-H bond.In comparing two enolates, the one with more substituents around the C=C double bond is lower in energy and is called the  _______ enolate. When a base is added to a carbonyl without an electronegative atom (as with aldehydes and ketones), an enolate is formed. This enolate undergoes nucleophilic  _______. The formation of an enolate is an acid-base equilibrium, so the  _______  the base, the more enolate that forms.A  _______ enolate is formed with a strong, nonnucleophilic base in a polar aprotic solvent at low temperatures.Nucleophilic  _______ occurs when there is an electronegative atom on the carbonyl carbon (as with carboxylic acids and their derivatives).The  _______  tautomer has an O-H group bonded to a C=C.Enolates are formed when  _______ a proton on the α carbon to a carbonyl group.In comparing two enolates, the one that is formed more rapidly is called the  _______ enolate.

FREE Expert Solution

1) The tautomer keto has a C=O and an additional C-H bond.

2) In comparing two enolates, the one with more substituents around the C=C double bond is lower in energy and is called the thermodynamic enolate. 

3) When a base is added to a carbonyl without an electronegative atom (as with aldehydes and ketones), an enolate is formed. This enolate undergoes nucleophilic  Addition

4) The formation of an enolate is an acid-base equilibrium, so the stronger the base, the more enolate that forms.

5) A  weaker enolate is formed with a strong, nonnucleophilic base in a polar aprotic solvent at low temperatures.


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Problem Details

Select the keyword or phrase that will best complete each sentence. 

Key terms:

addition        a base removes        weaker        enol        keto        thermodynamic        

stronger        an acid adds        acyl substitution        kinetic


The tautomer _______ has a C=O and an additional C-H bond.

In comparing two enolates, the one with more substituents around the C=C double bond is lower in energy and is called the  _______ enolate. 

When a base is added to a carbonyl without an electronegative atom (as with aldehydes and ketones), an enolate is formed. This enolate undergoes nucleophilic  _______. 

The formation of an enolate is an acid-base equilibrium, so the  _______  the base, the more enolate that forms.

A  _______ enolate is formed with a strong, nonnucleophilic base in a polar aprotic solvent at low temperatures.

Nucleophilic  _______ occurs when there is an electronegative atom on the carbonyl carbon (as with carboxylic acids and their derivatives).

The  _______  tautomer has an O-H group bonded to a C=C.

Enolates are formed when  _______ a proton on the α carbon to a carbonyl group.

In comparing two enolates, the one that is formed more rapidly is called the  _______ enolate.