(a) Interpretation: The reaction to carry out the given synthesis by first converting the alcohol into a sulfonyl chloride is to be shown. Concept introduction: Sulfonyl chloride has the general form R-SO 2 Cl . When sulfonyl chloride is treated with an alcohol, a sulfonate ester is produced via a sulfonation reaction. In the mechanism of sulfonation reaction, the alcohol attacks the sulfonyl chloride in a nucleophilic addition-elimination sequence. The nucleophilic OH group attacks the S=O group of the sulfonyl chlorides. In the second step, pyridine is added to the reaction for deprotonation. Nucleophilic elimination takes place in the third step. An alcohol changes a poor HO - leaving group into a great RSO 3 - leaving group in sulfonation step. Sulfonation of an alcohol occurs with retention of configuration at the C-OH carbon. Subsequent substitution or elimination reaction gives the target molecule.

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Answer 1

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Chapter 21, Problem 21.50P

Interpretation Introduction

(a)

Interpretation:

The reaction to carry out the given synthesis by first converting the alcohol into a sulfonyl chloride is to be shown.

Concept introduction:

Sulfonyl chloride has the general form R-SO2Cl. When sulfonyl chloride is treated with an alcohol, a sulfonate ester is produced via a sulfonation reaction. In the mechanism of sulfonation reaction, the alcohol attacks the sulfonyl chloride in a nucleophilic addition-elimination sequence. The nucleophilic OH group attacks the S=O group of the sulfonyl chlorides. In the second step, pyridine is added to the reaction for deprotonation. Nucleophilic elimination takes place in the third step. An alcohol changes a poor HO- leaving group into a great RSO3- leaving group in sulfonation step. Sulfonation of an alcohol occurs with retention of configuration at the C-OH carbon. Subsequent substitution or elimination reaction gives the target molecule.

Interpretation Introduction

(b)

Interpretation:

The reaction to carry out the given synthesis by first converting the alcohol into a sulfonyl chloride is to be shown.

Concept introduction:

Sulfonyl chloride has the general form R-SO2Cl. When sulfonyl chloride is treated with an alcohol, a sulfonate ester is produced via a sulfonation reaction. In the mechanism of sulfonation reaction, the alcohol attacks the sulfonyl chloride in a nucleophilic addition-elimination sequence. The nucleophilic OH group attacks the S=O group of the sulfonyl chlorides. In the second step, pyridine is added to the reaction for deprotonation. Nucleophilic elimination takes place in the third step. An alcohol changes a poor HO- leaving group into a great RSO3- leaving group in sulfonation step. Sulfonation of an alcohol occurs with retention of configuration at the C-OH carbon. Subsequent substitution or elimination reaction gives the target molecule.

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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 21, Problem 21.50P

Interpretation Introduction

(a)

Interpretation:

The reaction to carry out the given synthesis by first converting the alcohol into a sulfonyl chloride is to be shown.

Concept introduction:

Sulfonyl chloride has the general form R-SO2Cl. When sulfonyl chloride is treated with an alcohol, a sulfonate ester is produced via a sulfonation reaction. In the mechanism of sulfonation reaction, the alcohol attacks the sulfonyl chloride in a nucleophilic addition-elimination sequence. The nucleophilic OH group attacks the S=O group of the sulfonyl chlorides. In the second step, pyridine is added to the reaction for deprotonation. Nucleophilic elimination takes place in the third step. An alcohol changes a poor HO- leaving group into a great RSO3- leaving group in sulfonation step. Sulfonation of an alcohol occurs with retention of configuration at the C-OH carbon. Subsequent substitution or elimination reaction gives the target molecule.

Interpretation Introduction

(b)

Interpretation:

The reaction to carry out the given synthesis by first converting the alcohol into a sulfonyl chloride is to be shown.

Concept introduction:

Sulfonyl chloride has the general form R-SO2Cl. When sulfonyl chloride is treated with an alcohol, a sulfonate ester is produced via a sulfonation reaction. In the mechanism of sulfonation reaction, the alcohol attacks the sulfonyl chloride in a nucleophilic addition-elimination sequence. The nucleophilic OH group attacks the S=O group of the sulfonyl chlorides. In the second step, pyridine is added to the reaction for deprotonation. Nucleophilic elimination takes place in the third step. An alcohol changes a poor HO- leaving group into a great RSO3- leaving group in sulfonation step. Sulfonation of an alcohol occurs with retention of configuration at the C-OH carbon. Subsequent substitution or elimination reaction gives the target molecule.

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Answer 3

Question

Chapter 21, Problem 21.50P

Interpretation Introduction

(a)

Interpretation:

The reaction to carry out the given synthesis by first converting the alcohol into a sulfonyl chloride is to be shown.

Concept introduction:

Sulfonyl chloride has the general form R-SO2Cl. When sulfonyl chloride is treated with an alcohol, a sulfonate ester is produced via a sulfonation reaction. In the mechanism of sulfonation reaction, the alcohol attacks the sulfonyl chloride in a nucleophilic addition-elimination sequence. The nucleophilic OH group attacks the S=O group of the sulfonyl chlorides. In the second step, pyridine is added to the reaction for deprotonation. Nucleophilic elimination takes place in the third step. An alcohol changes a poor HO- leaving group into a great RSO3- leaving group in sulfonation step. Sulfonation of an alcohol occurs with retention of configuration at the C-OH carbon. Subsequent substitution or elimination reaction gives the target molecule.

Interpretation Introduction

(b)

Interpretation:

The reaction to carry out the given synthesis by first converting the alcohol into a sulfonyl chloride is to be shown.

Concept introduction:

Sulfonyl chloride has the general form R-SO2Cl. When sulfonyl chloride is treated with an alcohol, a sulfonate ester is produced via a sulfonation reaction. In the mechanism of sulfonation reaction, the alcohol attacks the sulfonyl chloride in a nucleophilic addition-elimination sequence. The nucleophilic OH group attacks the S=O group of the sulfonyl chlorides. In the second step, pyridine is added to the reaction for deprotonation. Nucleophilic elimination takes place in the third step. An alcohol changes a poor HO- leaving group into a great RSO3- leaving group in sulfonation step. Sulfonation of an alcohol occurs with retention of configuration at the C-OH carbon. Subsequent substitution or elimination reaction gives the target molecule.

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Answer 4

Question

Chapter 21, Problem 21.50P

Interpretation Introduction

(a)

Interpretation:

The reaction to carry out the given synthesis by first converting the alcohol into a sulfonyl chloride is to be shown.

Concept introduction:

Sulfonyl chloride has the general form R-SO2Cl. When sulfonyl chloride is treated with an alcohol, a sulfonate ester is produced via a sulfonation reaction. In the mechanism of sulfonation reaction, the alcohol attacks the sulfonyl chloride in a nucleophilic addition-elimination sequence. The nucleophilic OH group attacks the S=O group of the sulfonyl chlorides. In the second step, pyridine is added to the reaction for deprotonation. Nucleophilic elimination takes place in the third step. An alcohol changes a poor HO- leaving group into a great RSO3- leaving group in sulfonation step. Sulfonation of an alcohol occurs with retention of configuration at the C-OH carbon. Subsequent substitution or elimination reaction gives the target molecule.

Interpretation Introduction

(b)

Interpretation:

The reaction to carry out the given synthesis by first converting the alcohol into a sulfonyl chloride is to be shown.

Concept introduction:

Sulfonyl chloride has the general form R-SO2Cl. When sulfonyl chloride is treated with an alcohol, a sulfonate ester is produced via a sulfonation reaction. In the mechanism of sulfonation reaction, the alcohol attacks the sulfonyl chloride in a nucleophilic addition-elimination sequence. The nucleophilic OH group attacks the S=O group of the sulfonyl chlorides. In the second step, pyridine is added to the reaction for deprotonation. Nucleophilic elimination takes place in the third step. An alcohol changes a poor HO- leaving group into a great RSO3- leaving group in sulfonation step. Sulfonation of an alcohol occurs with retention of configuration at the C-OH carbon. Subsequent substitution or elimination reaction gives the target molecule.

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Answer 5

Chapter 21, Problem 21.50P

Interpretation Introduction

(a)

Interpretation:

The reaction to carry out the given synthesis by first converting the alcohol into a sulfonyl chloride is to be shown.

Concept introduction:

Sulfonyl chloride has the general form R-SO2Cl. When sulfonyl chloride is treated with an alcohol, a sulfonate ester is produced via a sulfonation reaction. In the mechanism of sulfonation reaction, the alcohol attacks the sulfonyl chloride in a nucleophilic addition-elimination sequence. The nucleophilic OH group attacks the S=O group of the sulfonyl chlorides. In the second step, pyridine is added to the reaction for deprotonation. Nucleophilic elimination takes place in the third step. An alcohol changes a poor HO- leaving group into a great RSO3- leaving group in sulfonation step. Sulfonation of an alcohol occurs with retention of configuration at the C-OH carbon. Subsequent substitution or elimination reaction gives the target molecule.

Interpretation Introduction

(b)

Interpretation:

The reaction to carry out the given synthesis by first converting the alcohol into a sulfonyl chloride is to be shown.

Concept introduction:

Sulfonyl chloride has the general form R-SO2Cl. When sulfonyl chloride is treated with an alcohol, a sulfonate ester is produced via a sulfonation reaction. In the mechanism of sulfonation reaction, the alcohol attacks the sulfonyl chloride in a nucleophilic addition-elimination sequence. The nucleophilic OH group attacks the S=O group of the sulfonyl chlorides. In the second step, pyridine is added to the reaction for deprotonation. Nucleophilic elimination takes place in the third step. An alcohol changes a poor HO- leaving group into a great RSO3- leaving group in sulfonation step. Sulfonation of an alcohol occurs with retention of configuration at the C-OH carbon. Subsequent substitution or elimination reaction gives the target molecule.

Answer 6

Chapter 21, Problem 21.50P

Interpretation Introduction

(a)

Interpretation:

The reaction to carry out the given synthesis by first converting the alcohol into a sulfonyl chloride is to be shown.

Concept introduction:

Sulfonyl chloride has the general form R-SO2Cl. When sulfonyl chloride is treated with an alcohol, a sulfonate ester is produced via a sulfonation reaction. In the mechanism of sulfonation reaction, the alcohol attacks the sulfonyl chloride in a nucleophilic addition-elimination sequence. The nucleophilic OH group attacks the S=O group of the sulfonyl chlorides. In the second step, pyridine is added to the reaction for deprotonation. Nucleophilic elimination takes place in the third step. An alcohol changes a poor HO- leaving group into a great RSO3- leaving group in sulfonation step. Sulfonation of an alcohol occurs with retention of configuration at the C-OH carbon. Subsequent substitution or elimination reaction gives the target molecule.

Answer 7

Chapter 21, Problem 21.50P

Interpretation Introduction

(a)

Interpretation:

The reaction to carry out the given synthesis by first converting the alcohol into a sulfonyl chloride is to be shown.

Concept introduction:

Sulfonyl chloride has the general form R-SO2Cl. When sulfonyl chloride is treated with an alcohol, a sulfonate ester is produced via a sulfonation reaction. In the mechanism of sulfonation reaction, the alcohol attacks the sulfonyl chloride in a nucleophilic addition-elimination sequence. The nucleophilic OH group attacks the S=O group of the sulfonyl chlorides. In the second step, pyridine is added to the reaction for deprotonation. Nucleophilic elimination takes place in the third step. An alcohol changes a poor HO- leaving group into a great RSO3- leaving group in sulfonation step. Sulfonation of an alcohol occurs with retention of configuration at the C-OH carbon. Subsequent substitution or elimination reaction gives the target molecule.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The reaction to carry out the given synthesis by first converting the alcohol into a sulfonyl chloride is to be shown.

Concept introduction:

Sulfonyl chloride has the general form R-SO2Cl. When sulfonyl chloride is treated with an alcohol, a sulfonate ester is produced via a sulfonation reaction. In the mechanism of sulfonation reaction, the alcohol attacks the sulfonyl chloride in a nucleophilic addition-elimination sequence. The nucleophilic OH group attacks the S=O group of the sulfonyl chlorides. In the second step, pyridine is added to the reaction for deprotonation. Nucleophilic elimination takes place in the third step. An alcohol changes a poor HO- leaving group into a great RSO3- leaving group in sulfonation step. Sulfonation of an alcohol occurs with retention of configuration at the C-OH carbon. Subsequent substitution or elimination reaction gives the target molecule.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The reaction to carry out the given synthesis by first converting the alcohol into a sulfonyl chloride is to be shown.

Concept introduction:

Sulfonyl chloride has the general form R-SO2Cl. When sulfonyl chloride is treated with an alcohol, a sulfonate ester is produced via a sulfonation reaction. In the mechanism of sulfonation reaction, the alcohol attacks the sulfonyl chloride in a nucleophilic addition-elimination sequence. The nucleophilic OH group attacks the S=O group of the sulfonyl chlorides. In the second step, pyridine is added to the reaction for deprotonation. Nucleophilic elimination takes place in the third step. An alcohol changes a poor HO- leaving group into a great RSO3- leaving group in sulfonation step. Sulfonation of an alcohol occurs with retention of configuration at the C-OH carbon. Subsequent substitution or elimination reaction gives the target molecule.

Answer 10

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Answer 13

Ch. 21 - Prob. 21.1P Ch. 21 - Prob. 21.2P Ch. 21 - Prob. 21.3P Ch. 21 - Prob. 21.4P Ch. 21 - Prob. 21.5P Ch. 21 - Prob. 21.6P Ch. 21 - Prob. 21.7P Ch. 21 - Prob. 21.8P Ch. 21 - Prob. 21.9P Ch. 21 - Prob. 21.10P

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Chapter 21 Solutions