It is to be explained why most ketones and aldehydes exist primarily in their keto forms but Propanedial exists primarily (>99%) in its enol form. Concept introduction: As a ketone or aldehyde, the species is called the keto form. In the enol form, the species has a carbon atom that is simultaneously a part of a C = C bond, characteristic of an alkene , and is bonded to OH, characteristic of an alcohol. In the keto form, there is a hydrogen atom on the carbon atom that is adjacent to the C = O group, so called alpha carbon, whereas in the enol form, the hydrogen appears on the oxygen atom instead. In a keto-enol tautomerization, the keto form is in equilibrium with its enol form via proton transfer steps. In general, keto form is more stable than enol because the total bond energy for the keto form is roughly greater than that of the enol form.

Question

Want to see the full answer?

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 7, Problem 7.43P

Interpretation Introduction

Interpretation:

It is to be explained why most ketones and aldehydes exist primarily in their keto forms but Propanedial exists primarily (>99%) in its enol form.

Concept introduction:

As a ketone or aldehyde, the species is called the keto form. In the enol form, the species has a carbon atom that is simultaneously a part of a C = C bond, characteristic of an alkene, and is bonded to OH, characteristic of an alcohol. In the keto form, there is a hydrogen atom on the carbon atom that is adjacent to the C = O group, so called alpha carbon, whereas in the enol form, the hydrogen appears on the oxygen atom instead. In a keto-enol tautomerization, the keto form is in equilibrium with its enol form via proton transfer steps. In general, keto form is more stable than enol because the total bond energy for the keto form is roughly greater than that of the enol form.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

What are the IUPAC Names of all the compounds in the picture?

1) a) Give the dominant Intermolecular Force (IMF) in a sample of each of the following compounds. Please show your work. (8) SF2, CH,OH, C₂H₂ b) Based on your answers given above, list the compounds in order of their Boiling Point from low to high. (8)

19.78 Write the products of the following sequences of reactions. Refer to your reaction road- maps to see how the combined reactions allow you to "navigate" between the different functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18 roadmaps along with your new Chapter 19 roadmap for these. (a) 1. BHS 2. H₂O₂ 3. H₂CrO4 4. SOCI₂ (b) 1. Cl₂/hv 2. KOLBU 3. H₂O, catalytic H₂SO4 4. H₂CrO4 Reaction Roadmap An alkene 5. EtOH 6.0.5 Equiv. NaOEt/EtOH 7. Mild H₂O An alkane 1.0 2. (CH3)₂S 3. H₂CrO (d) (c) 4. Excess EtOH, catalytic H₂SO OH 4. Mild H₂O* 5.0.5 Equiv. NaOEt/EtOH An alkene 6. Mild H₂O* A carboxylic acid 7. Mild H₂O* 1. SOC₁₂ 2. EtOH 3.0.5 Equiv. NaOEt/E:OH 5.1.0 Equiv. NaOEt 6. NH₂ (e) 1. 0.5 Equiv. NaOEt/EtOH 2. Mild H₂O* Br (f) i H An aldehyde 1. Catalytic NaOE/EtOH 2. H₂O*, heat 3. (CH,CH₂)₂Culi 4. Mild H₂O* 5.1.0 Equiv. LDA Br An ester 4. NaOH, H₂O 5. Mild H₂O* 6. Heat 7. MgBr 8. Mild H₂O* 7. Mild H₂O+

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 7, Problem 7.43P

Interpretation Introduction

Interpretation:

It is to be explained why most ketones and aldehydes exist primarily in their keto forms but Propanedial exists primarily (>99%) in its enol form.

Concept introduction:

As a ketone or aldehyde, the species is called the keto form. In the enol form, the species has a carbon atom that is simultaneously a part of a C = C bond, characteristic of an alkene, and is bonded to OH, characteristic of an alcohol. In the keto form, there is a hydrogen atom on the carbon atom that is adjacent to the C = O group, so called alpha carbon, whereas in the enol form, the hydrogen appears on the oxygen atom instead. In a keto-enol tautomerization, the keto form is in equilibrium with its enol form via proton transfer steps. In general, keto form is more stable than enol because the total bond energy for the keto form is roughly greater than that of the enol form.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 7, Problem 7.43P

Interpretation Introduction

Interpretation:

It is to be explained why most ketones and aldehydes exist primarily in their keto forms but Propanedial exists primarily (>99%) in its enol form.

Concept introduction:

As a ketone or aldehyde, the species is called the keto form. In the enol form, the species has a carbon atom that is simultaneously a part of a C = C bond, characteristic of an alkene, and is bonded to OH, characteristic of an alcohol. In the keto form, there is a hydrogen atom on the carbon atom that is adjacent to the C = O group, so called alpha carbon, whereas in the enol form, the hydrogen appears on the oxygen atom instead. In a keto-enol tautomerization, the keto form is in equilibrium with its enol form via proton transfer steps. In general, keto form is more stable than enol because the total bond energy for the keto form is roughly greater than that of the enol form.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 7, Problem 7.43P

Interpretation Introduction