Each step in the mechanism of the acid-catalysed interconversion of (R)-and (S)- 3 -methylpentan- 2 -one is to be shown. Concept introduction: In acid catalysed keto-enol tautomerism, the carbonyl oxygen is protonated by an acid. In the next step, deprotonation occurs at the alpha carbon to give the enol form. This is applicable on most of the proton-transfer mechanisms.

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 22.2A, Problem 22.2P

(a)

Interpretation Introduction

Interpretation:

Each step in the mechanism of the acid-catalysed interconversion of (R)-and (S)-3-methylpentan-2-one is to be shown.

Concept introduction:

In acid catalysed keto-enol tautomerism, the carbonyl oxygen is protonated by an acid. In the next step, deprotonation occurs at the alpha carbon to give the enol form. This is applicable on most of the proton-transfer mechanisms.

(b)

Interpretation Introduction

Interpretation:

A mechanism for the isomerization that occurs when cis-2,4-dimethylcyclohexanone is dissolved in aqueous ethanol containing a trace of NaOH is to be proposed.

Concept introduction:

In base catalysed keto-enol tautomerism, the proton is removed from the alpha carbon. In the next step, reprotonation occurs at oxygen to give a vinyl alcohol (enol form). Ketones and aldehydes act as weak proton acids in the presence of strong bases.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Draw the major organic substitution product(s) for (2R,3S)-2-bromo-3-methylpentane reacting with the given nucleophile. İndicate the stereochemistry, including H's, at each stereogenic center. Omit any byproducts. Н Br CH3CH2O (conc.)

From the table of available reagents select the one(s) you would use to convert 1-phenylethanol to acetophenone (PHCOCH3) Use the minimum number of steps; in no case are more than two steps necessary. List reagents by letter in the order that they are used; example: fa. Reagents available g. а. ВНз, ТHF: then H2O2, -OH d. PhMgBr; KMNO4, H2O then H30+ e. LIAIH4; h. POCI3, pyridine b. Br2, FeBr3 then H30+ c. CH3MgBr; f. PCC, then H3 0+ CH2 Cl2

From the table of available reagents select the one(s) you would use to convert cyclohexanone to the following compound: CH₂ Use the minimum number of steps; from one to five are required. List reagents by letter in the order that they are used; example: fa. Reagents Available a. BH3, THF; followed by H₂O2, OH g. Na* -CH(CO₂C₂H5) (from CH₂(CO₂C2H5)2 + Na* -OC₂H5) h. PBr3 i. PhCH₂Br b. Br₂, CH3CO₂H c. HCN, KCN d. H3O*, heat e. LDA (lithium diisopropylamide) f. NaBH4 j. Ph3P+-CH₂ k. pyridine, heat I. PhBr

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 22.2A, Problem 22.2P

(a)

Interpretation Introduction

Interpretation:

Each step in the mechanism of the acid-catalysed interconversion of (R)-and (S)-3-methylpentan-2-one is to be shown.

Concept introduction:

In acid catalysed keto-enol tautomerism, the carbonyl oxygen is protonated by an acid. In the next step, deprotonation occurs at the alpha carbon to give the enol form. This is applicable on most of the proton-transfer mechanisms.

(b)

Interpretation Introduction

Interpretation:

A mechanism for the isomerization that occurs when cis-2,4-dimethylcyclohexanone is dissolved in aqueous ethanol containing a trace of NaOH is to be proposed.

Concept introduction:

In base catalysed keto-enol tautomerism, the proton is removed from the alpha carbon. In the next step, reprotonation occurs at oxygen to give a vinyl alcohol (enol form). Ketones and aldehydes act as weak proton acids in the presence of strong bases.

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 22.2A, Problem 22.2P

(a)

Interpretation Introduction

Interpretation:

Each step in the mechanism of the acid-catalysed interconversion of (R)-and (S)-3-methylpentan-2-one is to be shown.

Concept introduction:

In acid catalysed keto-enol tautomerism, the carbonyl oxygen is protonated by an acid. In the next step, deprotonation occurs at the alpha carbon to give the enol form. This is applicable on most of the proton-transfer mechanisms.

(b)

Interpretation Introduction

Interpretation:

A mechanism for the isomerization that occurs when cis-2,4-dimethylcyclohexanone is dissolved in aqueous ethanol containing a trace of NaOH is to be proposed.

Concept introduction:

In base catalysed keto-enol tautomerism, the proton is removed from the alpha carbon. In the next step, reprotonation occurs at oxygen to give a vinyl alcohol (enol form). Ketones and aldehydes act as weak proton acids in the presence of strong bases.

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 22.2A, Problem 22.2P

(a)

Interpretation Introduction