a) Interpretation: How to prepare the diol shown is to be stated. Concept introduction: A cis diol can be prepared by treating an alkene with osmium tetroxide. The addition of osmium tetroxide in to the alkene takes place with syn stereochemistry to produce a cyclic osmic ester which when cleaved using NaHSO 3 yields the cis diol. A trans diol can be prepared by acid catalyzed ring opening of epoxides with anti stereochemistry. The acid protonates the epoxide and then water attacks the protonated epoxide from the less hindered side to form an intermediate which deprotonates to yield a trans diol. To state: How to prepare the diol shown.

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Answer 1

Question

Chapter 18.6, Problem 13P

Interpretation Introduction

a)

Interpretation:

How to prepare the diol shown is to be stated.

Concept introduction:

A cis diol can be prepared by treating an alkene with osmium tetroxide. The addition of osmium tetroxide in to the alkene takes place with syn stereochemistry to produce a cyclic osmic ester which when cleaved using NaHSO₃ yields the cis diol.

A trans diol can be prepared by acid catalyzed ring opening of epoxides with anti stereochemistry. The acid protonates the epoxide and then water attacks the protonated epoxide from the less hindered side to form an intermediate which deprotonates to yield a trans diol.

To state:

How to prepare the diol shown.

Interpretation Introduction

b)

Interpretation:

How to prepare the diol shown is to be stated.

Concept introduction:

A cis diol can be prepared by treating an alkene with osmium tetroxide. The addition of osmium tetroxide in to the alkene takes place with syn stereochemistry to produce a cyclic osmic ester which when cleaved using NaHSO₃ yields the cis diol.

A trans diol can be prepared by acid catalyzed ring opening of epoxides with anti stereochemistry. The acid protonates the epoxide and then water attacks the protonated epoxide from the less hindered side to form an intermediate which deprotonates to yield a trans diol.

To state:

How to prepare the diol shown.

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2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled** Peak Chemical Shift (d) 5.7 1 Multiplicity multiplate .......... 5.04 double of doublet 2 4.98 double of doublet 3 4.05 doublet of quartet 4 5 LO 3.80 quartet 1.3 doublet 6 Peak Chemical Shift (d) Multiplicity

Interpreting NMR spectra is a skill that often requires some amount of practice, which, in turn, necessitates access to a collection of NMR spectra. Beyond Labz Organic Synthesis and Organic Qualitative Analysis have spectral libraries containing over 700 1H NMR spectra. In this assignment, you will take advantage of this by first predicting the NMR spectra for two closely related compounds and then checking your predictions by looking up the actual spectra in the spectra library. After completing this assignment, you may wish to select other compounds for additional practice. 1. Write the IUPAC names for the following two structures: Question 2 Question 3 2. Predict the NMR spectra for each of these two compounds by listing, in the NMR tables below, the chemical shift, the splitting, and the number of hydrogens associated with each predicted peak. Sort the peaks from largest chemical shift to lowest. **Not all slots must be filled**

11:14 ... worksheets.beyondlabz.com 3. To check your predictions, click this link for Interpreting NMR Spectra 1. You will see a list of all the - compounds in the spectra library in alphabetical order by IUPAC name. Hovering over a name in the list will show the structure on the chalkboard. The four buttons on the top of the Spectra tab in the tray are used to select the different spectroscopic techniques for the selected compound. Make sure the NMR button has been selected. 4. Scroll through the list of names to find the names for the two compounds you have been given and click on the name to display the NMR spectrum for each. In the NMR tables below, list the chemical shift, the splitting, and the number of hydrogens associated with each peak for each compound. Compare your answers to your predictions. **Not all slots must be filled** Peak Chemical Shift (d) Multiplicity 1 2 3 4 5

Answer 2

Question

Chapter 18.6, Problem 13P

Interpretation Introduction

a)

Interpretation:

How to prepare the diol shown is to be stated.

Concept introduction:

A cis diol can be prepared by treating an alkene with osmium tetroxide. The addition of osmium tetroxide in to the alkene takes place with syn stereochemistry to produce a cyclic osmic ester which when cleaved using NaHSO₃ yields the cis diol.

A trans diol can be prepared by acid catalyzed ring opening of epoxides with anti stereochemistry. The acid protonates the epoxide and then water attacks the protonated epoxide from the less hindered side to form an intermediate which deprotonates to yield a trans diol.

To state:

How to prepare the diol shown.

Interpretation Introduction

b)

Interpretation:

How to prepare the diol shown is to be stated.

Concept introduction:

A cis diol can be prepared by treating an alkene with osmium tetroxide. The addition of osmium tetroxide in to the alkene takes place with syn stereochemistry to produce a cyclic osmic ester which when cleaved using NaHSO₃ yields the cis diol.

A trans diol can be prepared by acid catalyzed ring opening of epoxides with anti stereochemistry. The acid protonates the epoxide and then water attacks the protonated epoxide from the less hindered side to form an intermediate which deprotonates to yield a trans diol.

To state:

How to prepare the diol shown.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 18.6, Problem 13P

Interpretation Introduction

a)

Interpretation:

How to prepare the diol shown is to be stated.

Concept introduction:

A cis diol can be prepared by treating an alkene with osmium tetroxide. The addition of osmium tetroxide in to the alkene takes place with syn stereochemistry to produce a cyclic osmic ester which when cleaved using NaHSO₃ yields the cis diol.

A trans diol can be prepared by acid catalyzed ring opening of epoxides with anti stereochemistry. The acid protonates the epoxide and then water attacks the protonated epoxide from the less hindered side to form an intermediate which deprotonates to yield a trans diol.

To state:

How to prepare the diol shown.

Interpretation Introduction

b)

Interpretation:

How to prepare the diol shown is to be stated.

Concept introduction:

A cis diol can be prepared by treating an alkene with osmium tetroxide. The addition of osmium tetroxide in to the alkene takes place with syn stereochemistry to produce a cyclic osmic ester which when cleaved using NaHSO₃ yields the cis diol.

A trans diol can be prepared by acid catalyzed ring opening of epoxides with anti stereochemistry. The acid protonates the epoxide and then water attacks the protonated epoxide from the less hindered side to form an intermediate which deprotonates to yield a trans diol.

To state:

How to prepare the diol shown.

Expert Solution & Answer

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See solution

Answer 4

Question

Chapter 18.6, Problem 13P

Interpretation Introduction

a)

Interpretation:

How to prepare the diol shown is to be stated.

Concept introduction:

A cis diol can be prepared by treating an alkene with osmium tetroxide. The addition of osmium tetroxide in to the alkene takes place with syn stereochemistry to produce a cyclic osmic ester which when cleaved using NaHSO₃ yields the cis diol.

A trans diol can be prepared by acid catalyzed ring opening of epoxides with anti stereochemistry. The acid protonates the epoxide and then water attacks the protonated epoxide from the less hindered side to form an intermediate which deprotonates to yield a trans diol.

To state:

How to prepare the diol shown.

Interpretation Introduction

b)

Interpretation:

How to prepare the diol shown is to be stated.

Concept introduction:

A cis diol can be prepared by treating an alkene with osmium tetroxide. The addition of osmium tetroxide in to the alkene takes place with syn stereochemistry to produce a cyclic osmic ester which when cleaved using NaHSO₃ yields the cis diol.

A trans diol can be prepared by acid catalyzed ring opening of epoxides with anti stereochemistry. The acid protonates the epoxide and then water attacks the protonated epoxide from the less hindered side to form an intermediate which deprotonates to yield a trans diol.

To state:

How to prepare the diol shown.

Expert Solution & Answer

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Answer 5

Chapter 18.6, Problem 13P

Interpretation Introduction

a)

Interpretation:

How to prepare the diol shown is to be stated.

Concept introduction:

A cis diol can be prepared by treating an alkene with osmium tetroxide. The addition of osmium tetroxide in to the alkene takes place with syn stereochemistry to produce a cyclic osmic ester which when cleaved using NaHSO₃ yields the cis diol.

A trans diol can be prepared by acid catalyzed ring opening of epoxides with anti stereochemistry. The acid protonates the epoxide and then water attacks the protonated epoxide from the less hindered side to form an intermediate which deprotonates to yield a trans diol.

To state:

How to prepare the diol shown.

Interpretation Introduction

b)

Interpretation:

How to prepare the diol shown is to be stated.

Concept introduction:

A cis diol can be prepared by treating an alkene with osmium tetroxide. The addition of osmium tetroxide in to the alkene takes place with syn stereochemistry to produce a cyclic osmic ester which when cleaved using NaHSO₃ yields the cis diol.

A trans diol can be prepared by acid catalyzed ring opening of epoxides with anti stereochemistry. The acid protonates the epoxide and then water attacks the protonated epoxide from the less hindered side to form an intermediate which deprotonates to yield a trans diol.

To state:

How to prepare the diol shown.

Answer 6

Chapter 18.6, Problem 13P

Interpretation Introduction

a)

Interpretation:

How to prepare the diol shown is to be stated.

Concept introduction:

A cis diol can be prepared by treating an alkene with osmium tetroxide. The addition of osmium tetroxide in to the alkene takes place with syn stereochemistry to produce a cyclic osmic ester which when cleaved using NaHSO₃ yields the cis diol.

A trans diol can be prepared by acid catalyzed ring opening of epoxides with anti stereochemistry. The acid protonates the epoxide and then water attacks the protonated epoxide from the less hindered side to form an intermediate which deprotonates to yield a trans diol.

To state:

How to prepare the diol shown.

Answer 7

Chapter 18.6, Problem 13P

Interpretation Introduction

a)

Interpretation:

How to prepare the diol shown is to be stated.

Concept introduction:

A cis diol can be prepared by treating an alkene with osmium tetroxide. The addition of osmium tetroxide in to the alkene takes place with syn stereochemistry to produce a cyclic osmic ester which when cleaved using NaHSO₃ yields the cis diol.

A trans diol can be prepared by acid catalyzed ring opening of epoxides with anti stereochemistry. The acid protonates the epoxide and then water attacks the protonated epoxide from the less hindered side to form an intermediate which deprotonates to yield a trans diol.

To state:

How to prepare the diol shown.

Answer 8

Interpretation Introduction

b)

Interpretation:

How to prepare the diol shown is to be stated.

Concept introduction:

A cis diol can be prepared by treating an alkene with osmium tetroxide. The addition of osmium tetroxide in to the alkene takes place with syn stereochemistry to produce a cyclic osmic ester which when cleaved using NaHSO₃ yields the cis diol.

A trans diol can be prepared by acid catalyzed ring opening of epoxides with anti stereochemistry. The acid protonates the epoxide and then water attacks the protonated epoxide from the less hindered side to form an intermediate which deprotonates to yield a trans diol.

To state:

How to prepare the diol shown.

Answer 9

Interpretation Introduction

b)

Interpretation:

How to prepare the diol shown is to be stated.

Concept introduction:

A cis diol can be prepared by treating an alkene with osmium tetroxide. The addition of osmium tetroxide in to the alkene takes place with syn stereochemistry to produce a cyclic osmic ester which when cleaved using NaHSO₃ yields the cis diol.

A trans diol can be prepared by acid catalyzed ring opening of epoxides with anti stereochemistry. The acid protonates the epoxide and then water attacks the protonated epoxide from the less hindered side to form an intermediate which deprotonates to yield a trans diol.

To state:

How to prepare the diol shown.

Answer 10

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Answer 11

Expert Solution & Answer

Answer 12

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Answer 13

Ch. 18.1 - Name the following ethers:Ch. 18.2 - Why do you suppose only symmetrical ethers are...Ch. 18.2 - How would you prepare the following ethers using a...Ch. 18.2 - Review the mechanism of oxymercuration shown in...Ch. 18.2 - How would you prepare the following ethers? Use...Ch. 18.2 - Prob. 6P Ch. 18.3 - Prob. 7P Ch. 18.3 - Write the mechanism of the acid-induced cleavage...Ch. 18.3 - Why are HI and HBr more effective than HCl in...Ch. 18.4 - What product would you expect from Claisen...

Solution Summary: The author explains how a cis diol can be prepared by treating an alkene with osmium tetroxide.

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