Why an aldol condensation product is not formed when a 1,3-diketone such as 2,4-pentanedione is treated with a base is to be explained. Concept introduction: Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule. To explain: Why treatment of a 1,3-diketone such as 2,4-pentanedione does not give an aldol condensation product.

Question

Consider the following two acid-base reactions: OH OHI Based on what you know about the compounds and their acidity, which direction would you expect both of these reactions to proceed? Show your reasoning. A pKa table has been provided in case you need it. Functional group Example pka CHA -50 Alkane -35 Amine : NH3 Alkyne RH 25 Water HO-H 169 16 10 Protonated amines NH 10 5 Carboxylic acids OH Hydrochloric acid HCI A chemist intends to run the following reaction on the three substrates shown below: H₂O R-CI product room temp. Cl Cl (1) (2) (3) They find one will react quickly, one slowly, and one will not react at all. Which is which, and why? HINT: What is the reaction they're trying to do? Does that mechanism tell you anything about why something would be favored?

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 23.6, Problem 9P

Interpretation Introduction

Interpretation:

Why an aldol condensation product is not formed when a 1,3-diketone such as 2,4-pentanedione is treated with a base is to be explained.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule.

To explain:

Why treatment of a 1,3-diketone such as 2,4-pentanedione does not give an aldol condensation product.

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Consider the following two acid-base reactions: OH OHI Based on what you know about the compounds and their acidity, which direction would you expect both of these reactions to proceed? Show your reasoning. A pKa table has been provided in case you need it. Functional group Example pka CHA -50 Alkane -35 Amine : NH3 Alkyne RH 25 Water HO-H 169 16 10 Protonated amines NH 10 5 Carboxylic acids OH Hydrochloric acid HCI A chemist intends to run the following reaction on the three substrates shown below: H₂O R-CI product room temp. Cl Cl (1) (2) (3) They find one will react quickly, one slowly, and one will not react at all. Which is which, and why? HINT: What is the reaction they're trying to do? Does that mechanism tell you anything about why something would be favored?

NH3 decomposes through an equilibrium reaction between NH3, H2, and N2. Only one of the options is correct:(A). The mechanism of the NH3 decomposition reaction must necessarily involve the collision of two NH3 molecules to induce a rearrangement of the atoms in this molecule.(B). The molecular weight of the NH3 decomposition reaction is 2 since two NH3 molecules must collide.(C). The rate of the NH3 decomposition reaction must be greater than that of NH3 synthesis, since the former requires two molecules to collide and the latter, four.(D). The NH3 decomposition reaction cannot occur in a single step.

Given the equilibrium A2 + B2 ⇌ 2 AB where k1 is the rate coefficient of the forward reaction and k-1 is the rate coefficient of the reverse reaction, with the forward reaction being first-order in A2 and B2, and the reverse reaction being second-order in AB. Equilibrium will be reached later if the relative values of the constants are:(A) k1 high and k-1 high(B) k1 high and k-1 low(C) k1 low and k-1 high(D) k1 low and k-1 low

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 23.6, Problem 9P

Interpretation Introduction

Interpretation:

Why an aldol condensation product is not formed when a 1,3-diketone such as 2,4-pentanedione is treated with a base is to be explained.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule.

To explain:

Why treatment of a 1,3-diketone such as 2,4-pentanedione does not give an aldol condensation product.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook 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 23.6, Problem 9P

Interpretation Introduction

Interpretation:

Why an aldol condensation product is not formed when a 1,3-diketone such as 2,4-pentanedione is treated with a base is to be explained.

Concept introduction:

Aldehydes and ketones with α-hydrogen undergo a base catalyzed carbonyl condensation reaction in aldol condensation. In this reaction two molecules of the reactant combine by forming a bond between α-carbon of one molecule and the carbonyl carbon within the same molecule or of the second molecule.

To explain:

Why treatment of a 1,3-diketone such as 2,4-pentanedione does not give an aldol condensation product.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook 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 23.6, Problem 9P

Interpretation Introduction