(a) Interpretation: Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed. Concept introduction: The product has 10 carbon atoms while the starting material has four and two carbon atoms. This means that the reaction that alters the carbon skeleton must occur. The retrosynthetic approach suggests the reaction to be two back-to-back Diels-Alder reaction.

Question

יווי 10 20 30 40 50 60 70 3.5 3 2.5 2 1.5 1 [ppm] 3.5 3 2.5 2 1.5 1 6 [ppm] 1 1.5 -2.5 3.5

Answer 1

Question

Chapter 24, Problem 24.79P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This means that the reaction that alters the carbon skeleton must occur. The retrosynthetic approach suggests the reaction to be two back-to-back Diels-Alder reaction.

Interpretation Introduction

(b)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. Hence there must be one reaction that alters the carbon skeleton. Target product is a chain with OH functional group at the terminal position. Retrosynthetic approach suggests that the formation of the product through Diels-Alder reaction is followed by oxidative cleavage and reduction.

Interpretation Introduction

(c)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. This suggests that one reaction to alter carbon skeleton must occur. Retrosynthesis suggests the formation of β- hydroxy aldehyde via aldol reaction. The precursor for this reaction must be 1, 6-dialdehyde.

Interpretation Introduction

(d)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This suggests that two reactions that alter carbon skeleton must occur. The retrosynthesis of the target suggests it to be a product of Diels-Alder reaction. The two precursors of Diels alder reaction must be butadiene and an aldehyde.

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יווי 10 20 30 40 50 60 70 3.5 3 2.5 2 1.5 1 [ppm] 3.5 3 2.5 2 1.5 1 6 [ppm] 1 1.5 -2.5 3.5

2H2S(g)+3O2(g)→2SO2(g)+2H2O(g) A 1.2mol sample of H2S(g) is combined with excess O2(g), and the reaction goes to completion. Question Which of the following predicts the theoretical yield of SO2(g) from the reaction? Responses 1.2 g Answer A: 1.2 grams A 41 g Answer B: 41 grams B 77 g Answer C: 77 grams C 154 g Answer D: 154 grams D

Part VII. Below are the 'HNMR, 13 C-NMR, COSY 2D- NMR, and HSQC 2D-NMR (similar with HETCOR but axes are reversed) spectra of an organic compound with molecular formula C6H1003 - Assign chemical shift values to the H and c atoms of the compound. Find the structure. Show complete solutions. Predicted 1H NMR Spectrum 4.7 4.6 4.5 4.4 4.3 4.2 4.1 4.0 3.9 3.8 3.7 3.6 3.5 3.4 3.3 3.2 3.1 3.0 2.9 2.8 2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 f1 (ppm) Predicted 13C NMR Spectrum 100 f1 (ppm) 30 220 210 200 190 180 170 160 150 140 130 120 110 90 80 70 -26 60 50 40 46 30 20 115 10 1.0 0.9 0.8 0 -10

Answer 2

Question

Chapter 24, Problem 24.79P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This means that the reaction that alters the carbon skeleton must occur. The retrosynthetic approach suggests the reaction to be two back-to-back Diels-Alder reaction.

Interpretation Introduction

(b)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. Hence there must be one reaction that alters the carbon skeleton. Target product is a chain with OH functional group at the terminal position. Retrosynthetic approach suggests that the formation of the product through Diels-Alder reaction is followed by oxidative cleavage and reduction.

Interpretation Introduction

(c)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. This suggests that one reaction to alter carbon skeleton must occur. Retrosynthesis suggests the formation of β- hydroxy aldehyde via aldol reaction. The precursor for this reaction must be 1, 6-dialdehyde.

Interpretation Introduction

(d)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This suggests that two reactions that alter carbon skeleton must occur. The retrosynthesis of the target suggests it to be a product of Diels-Alder reaction. The two precursors of Diels alder reaction must be butadiene and an aldehyde.

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Answer 3

Question

Chapter 24, Problem 24.79P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This means that the reaction that alters the carbon skeleton must occur. The retrosynthetic approach suggests the reaction to be two back-to-back Diels-Alder reaction.

Interpretation Introduction

(b)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. Hence there must be one reaction that alters the carbon skeleton. Target product is a chain with OH functional group at the terminal position. Retrosynthetic approach suggests that the formation of the product through Diels-Alder reaction is followed by oxidative cleavage and reduction.

Interpretation Introduction

(c)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. This suggests that one reaction to alter carbon skeleton must occur. Retrosynthesis suggests the formation of β- hydroxy aldehyde via aldol reaction. The precursor for this reaction must be 1, 6-dialdehyde.

Interpretation Introduction

(d)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This suggests that two reactions that alter carbon skeleton must occur. The retrosynthesis of the target suggests it to be a product of Diels-Alder reaction. The two precursors of Diels alder reaction must be butadiene and an aldehyde.

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Answer 4

Question

Chapter 24, Problem 24.79P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This means that the reaction that alters the carbon skeleton must occur. The retrosynthetic approach suggests the reaction to be two back-to-back Diels-Alder reaction.

Interpretation Introduction

(b)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. Hence there must be one reaction that alters the carbon skeleton. Target product is a chain with OH functional group at the terminal position. Retrosynthetic approach suggests that the formation of the product through Diels-Alder reaction is followed by oxidative cleavage and reduction.

Interpretation Introduction

(c)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. This suggests that one reaction to alter carbon skeleton must occur. Retrosynthesis suggests the formation of β- hydroxy aldehyde via aldol reaction. The precursor for this reaction must be 1, 6-dialdehyde.

Interpretation Introduction

(d)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This suggests that two reactions that alter carbon skeleton must occur. The retrosynthesis of the target suggests it to be a product of Diels-Alder reaction. The two precursors of Diels alder reaction must be butadiene and an aldehyde.

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Answer 5

Chapter 24, Problem 24.79P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This means that the reaction that alters the carbon skeleton must occur. The retrosynthetic approach suggests the reaction to be two back-to-back Diels-Alder reaction.

Interpretation Introduction

(b)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. Hence there must be one reaction that alters the carbon skeleton. Target product is a chain with OH functional group at the terminal position. Retrosynthetic approach suggests that the formation of the product through Diels-Alder reaction is followed by oxidative cleavage and reduction.

Interpretation Introduction

(c)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. This suggests that one reaction to alter carbon skeleton must occur. Retrosynthesis suggests the formation of β- hydroxy aldehyde via aldol reaction. The precursor for this reaction must be 1, 6-dialdehyde.

Interpretation Introduction

(d)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This suggests that two reactions that alter carbon skeleton must occur. The retrosynthesis of the target suggests it to be a product of Diels-Alder reaction. The two precursors of Diels alder reaction must be butadiene and an aldehyde.

Answer 6

Chapter 24, Problem 24.79P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This means that the reaction that alters the carbon skeleton must occur. The retrosynthetic approach suggests the reaction to be two back-to-back Diels-Alder reaction.

Answer 7

Chapter 24, Problem 24.79P

Interpretation Introduction

(a)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This means that the reaction that alters the carbon skeleton must occur. The retrosynthetic approach suggests the reaction to be two back-to-back Diels-Alder reaction.

Answer 8

Interpretation Introduction

(b)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. Hence there must be one reaction that alters the carbon skeleton. Target product is a chain with OH functional group at the terminal position. Retrosynthetic approach suggests that the formation of the product through Diels-Alder reaction is followed by oxidative cleavage and reduction.

Answer 9

Interpretation Introduction

(b)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. Hence there must be one reaction that alters the carbon skeleton. Target product is a chain with OH functional group at the terminal position. Retrosynthetic approach suggests that the formation of the product through Diels-Alder reaction is followed by oxidative cleavage and reduction.

Answer 10

Interpretation Introduction

(c)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. This suggests that one reaction to alter carbon skeleton must occur. Retrosynthesis suggests the formation of β- hydroxy aldehyde via aldol reaction. The precursor for this reaction must be 1, 6-dialdehyde.

Answer 11

Interpretation Introduction

(c)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 6 carbon atoms while the starting material has four and two carbon atoms. This suggests that one reaction to alter carbon skeleton must occur. Retrosynthesis suggests the formation of β- hydroxy aldehyde via aldol reaction. The precursor for this reaction must be 1, 6-dialdehyde.

Answer 12

Interpretation Introduction

(d)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This suggests that two reactions that alter carbon skeleton must occur. The retrosynthesis of the target suggests it to be a product of Diels-Alder reaction. The two precursors of Diels alder reaction must be butadiene and an aldehyde.

Answer 13

Interpretation Introduction

(d)

Interpretation:

Synthesis of the following compound using ethene and buta-1, 3-diene as the only source of carbon is to be proposed.

Concept introduction:

The product has 10 carbon atoms while the starting material has four and two carbon atoms. This suggests that two reactions that alter carbon skeleton must occur. The retrosynthesis of the target suggests it to be a product of Diels-Alder reaction. The two precursors of Diels alder reaction must be butadiene and an aldehyde.

Answer 14

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Ch. 24 - Prob. 24.1P Ch. 24 - Prob. 24.2P Ch. 24 - Prob. 24.3P Ch. 24 - Prob. 24.4P Ch. 24 - Prob. 24.5P Ch. 24 - Prob. 24.6P Ch. 24 - Prob. 24.7P Ch. 24 - Prob. 24.8P Ch. 24 - Prob. 24.9P Ch. 24 - Prob. 24.10P

Chapter 24 Solutions