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The compound whose structure is shown here is acetyl acetone. It exists in two forms: the enol form and the keto form. The molecule reacts with OH – to form an anion, [CH 3 COCHCOCH 3 ] (often abbreviated acac – for acetylacetonate ion). One or the most interesting aspects of this anion is that one or more of them can react with transition metal cations to give stable, highly colored compounds. (a) Are the keto and enol forms of acetylacetone resonance forms? Explain your answer. (b) What is the hybridization or each atom (except H) in the enol form? What changes in hybridization occur when it is transformed into the keto form? (c) What are the electron-pair geometry and molecular geometry around each C atom in the keto and enol forms? What changes in geometry occur when the keto form changes to the enol form? (d) Draw three possible resonance structures for the acac – ion. (e) Is c is- trans isomerism possible in either the enol or the keto form of acetylacetone? (f) Is the enol form of acetylacetone polar? Where do the positive and negative charges lie in the molecule?

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Chemistry & Chemical Reactivity

9th Edition
John C. Kotz + 3 others
Publisher: Cengage Learning
ISBN: 9781133949640

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BuyFindarrow_forward

Chemistry & Chemical Reactivity

9th Edition
John C. Kotz + 3 others
Publisher: Cengage Learning
ISBN: 9781133949640
Chapter 9, Problem 54IL
Textbook Problem
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The compound whose structure is shown here is acetyl acetone. It exists in two forms: the enol form and the keto form.

Chapter 9, Problem 54IL, The compound whose structure is shown here is acetyl acetone. It exists in two forms: the enol form , example  1

The molecule reacts with OH to form an anion, [CH3COCHCOCH3] (often abbreviated acac for acetylacetonate ion). One or the most interesting aspects of this anion is that one or more of them can react with transition metal cations to give stable, highly colored compounds.

Chapter 9, Problem 54IL, The compound whose structure is shown here is acetyl acetone. It exists in two forms: the enol form , example  2

(a) Are the keto and enol forms of acetylacetone resonance forms? Explain your answer.

(b) What is the hybridization or each atom (except H) in the enol form? What changes in hybridization occur when it is transformed into the keto form?

(c) What are the electron-pair geometry and molecular geometry around each C atom in the keto and enol forms? What changes in geometry occur when the keto form changes to the enol form?

(d) Draw three possible resonance structures for the acac ion.

(e) Is cis-trans isomerism possible in either the enol or the keto form of acetylacetone?

(f) Is the enol form of acetylacetone polar? Where do the positive and negative charges lie in the molecule?

(a)

Interpretation Introduction

Interpretation:

Check whether the keto and enol form of acetylacetone are its resonance form or not.

Concept Introduction:

Resonance: These concepts explain bonding that describes the delocalization of electrons within the molecules.

Keto enol form: It is referred to a chemical equilibrium between a keto from enol, the both forms are said to be tautomer’s of each other.

Explanation of Solution

Given Keto-enol resonance form of acetylacetone is,

The acetylacetone is (2,4-pentadione) exists in two isomeric from shown below, the 2,4-pentanedione enol form shown is the more stable enol, since the loan pair on the enol oxygen can delocalize across the five atoms to the electronegative carbonyl carbon...

(b)

Interpretation Introduction

Interpretation:

The hybridization of each atoms in the enol form of acetylacetone and the possible changes occur when it is transformed into the keto form should be determined.

Concept Introduction:

Keto enol form: It is referred to a chemical equilibrium between a keto from enol, the both forms are said to be tautomer’s of each other.

Hybridization is the mixing of valence atomic orbitals to get equivalent hybridized orbitals that having similar characteristics and energy.

Geometry of a molecule can be predicted by knowing its hybridization.

Geometry of different types of molecule with respect to the hybridizations are mentioned are mentioned below,

TypeofmoleculeHybridaizationAtomicorbitalsusedforhybridaizationGeometryAX2sp1s+1pLinearAX3,AX2Bsp21s+2pTrigonalplanarAX4,AX3B,AX2B2sp31s+3pTetrahedralAX5,AX4B,AX3B2,AX2B3sp3d1s+3p+1dTrigonalbipyramidalAX6,AX5B,AX4B2sp3d21s+3p+2dOctahedralACentralatomXAtomsbondedtoABNonbondingelectronpairsonA

(c)

Interpretation Introduction

Interpretation:

Electron pair and molecular geometries around each C atom in the keto and enol forms have to be determined. The possible changes in geometry occur when the keto form changes to the enol form should be determined.

Concept Introduction:

Keto enol form: It is referred to a chemical equilibrium between a keto from enol, the both forms are said to be tautomer’s of each other.

Hybridization is the mixing of valence atomic orbitals to get equivalent hybridized orbitals that having similar characteristics and energy.

Geometry of a molecule can be predicted by knowing its hybridization.

Electron geometry is the shape of a molecule predicted by considering both bond electron pairs and lone pair of electrons.

Molecular geometry is the shape of a molecule predicted by considering only bond pair of electrons

Geometry of different types of molecule with respect to the hybridizations is mentioned are mentioned below,

TypeofmoleculeHybridaizationAtomicorbitalsusedforhybridaizationGeometryAX2sp1s+1pLinearAX3,AX2Bsp21s+2pTrigonalplanarAX4,AX3B,AX2B2sp31s+3pTetrahedralAX5,AX4B,AX3B2,AX2B3sp3d1s+3p+1dTrigonalbipyramidalAX6,AX5B,AX4B2sp3d21s+3p+2dOctahedralACentralatomXAtomsbondedtoABNonbondingelectronpairsonA

(d)

Interpretation Introduction

Interpretation:

Three possible resonance structures for the acetlyacetonate ion (acac) should be drawn.

Concept Introduction:

Keto enol form: It is referred to a chemical equilibrium between a keto from enol, the both forms are said to be tautomer’s of each other.

Resonance: These concepts explain bonding that describes the delocalization of electrons within the molecules.

(e)

Interpretation Introduction

Interpretation:

Check whether the tautomers of given compound shows cis-trans isomerism or not.

Concept Introduction:

Keto enol form: It is referred to a chemical equilibrium between a keto from enol, the both forms are said to be tautomer’s of each other.

The arrangement of groups attached to the carbo atoms involved in a C=C double bond leads to cis and trans isomers.

Isomer: The molecule has same molecular formula and attached for different functional groups it is called isomers.

Cis Isomer: The two groups attached on same side of C=C double bond irrespective of molecules or atoms is called cis isomer this type molecule has polar nature.

In cis isomer the hydrogen atoms are on the same side of the two carbon atom.

Chemistry & Chemical Reactivity, Chapter 9, Problem 54IL , additional homework tip  1

Trans isomer: The two groups are attached on opposite sides of the carbon-carbon double bond.

The hydrogen atoms are on the opposite side of the two carbon atom.

Chemistry & Chemical Reactivity, Chapter 9, Problem 54IL , additional homework tip  2

(f)

Interpretation Introduction

Interpretation:

Check whether the enol tautomer of given compound shows is polar or not. The position of positive and negative charges in the molecule has to be determined.

Concept Introduction:

Keto enol form: It is referred to a chemical equilibrium between a keto from enol, the both forms are said to be tautomer’s of each other.

The arrangement of groups attached to the carbo atoms involved in a C=C double bond leads to cis and trans isomers.

Polar molecule: It has net dipole as a result of the opposing charges for example molecule has partially positive charge and partially negative charge. It has slight positive charge on one side and a slight negative charge on the other side.

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Chemistry & Chemical Reactivity
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