The structure of sabinene and the other compound, which is formed in the ozonolysis of sabinene followed by hydrolysis in the presence of zinc, is to be given. Also, the structure of Δ 3 -carene , which gives compound B as a product of ozonolysis reaction, is to be given. Concept introduction: > Ozonolysis of alkenes produces carbonyl compounds. These carbonyl compounds can be formaldehyde, other aldehydes , or ketones , depending upon the structure of the alkene used in the reaction. > On ozonolysis, cyclic alkenes produce a single compound containing two carbonyl groups. > If formaldehyde is produced after ozonolysis, the alkene has a terminal double bond. > If an aldehyde is produced after ozonolysis, at least one of the double bonded carbon atoms in the alkene has a hydrogen attached to it. > If a ketone is produced after ozonolysis, at least one of the double bonded carbon atoms in the alkene must be disubstituted. > The total number of hydrogen and carbon atoms in the original alkene is equal to the total number of carbon and hydrogen atoms in two products formed in the ozonolysis reaction.

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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 8, Problem 60P

Interpretation Introduction

Interpretation:

The structure of sabinene and the other compound, which is formed in the ozonolysis of sabinene followed by hydrolysis in the presence of zinc, is to be given. Also, the structure of Δ3-carene, which gives compound B as a product of ozonolysis reaction, is to be given.

Concept introduction:
>
Ozonolysis of alkenes produces carbonyl compounds. These carbonyl compounds can be formaldehyde, other aldehydes, or ketones, depending upon the structure of the alkene used in the reaction.
>
On ozonolysis, cyclic alkenes produce a single compound containing two carbonyl groups.
>
If formaldehyde is produced after ozonolysis, the alkene has a terminal double bond.
>
If an aldehyde is produced after ozonolysis, at least one of the double bonded carbon atoms in the alkene has a hydrogen attached to it.
>
If a ketone is produced after ozonolysis, at least one of the double bonded carbon atoms in the alkene must be disubstituted.
>
The total number of hydrogen and carbon atoms in the original alkene is equal to the total number of carbon and hydrogen atoms in two products formed in the ozonolysis reaction.

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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

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 8, Problem 60P

Interpretation Introduction

Interpretation:

The structure of sabinene and the other compound, which is formed in the ozonolysis of sabinene followed by hydrolysis in the presence of zinc, is to be given. Also, the structure of Δ3-carene, which gives compound B as a product of ozonolysis reaction, is to be given.

Concept introduction:
>
Ozonolysis of alkenes produces carbonyl compounds. These carbonyl compounds can be formaldehyde, other aldehydes, or ketones, depending upon the structure of the alkene used in the reaction.
>
On ozonolysis, cyclic alkenes produce a single compound containing two carbonyl groups.
>
If formaldehyde is produced after ozonolysis, the alkene has a terminal double bond.
>
If an aldehyde is produced after ozonolysis, at least one of the double bonded carbon atoms in the alkene has a hydrogen attached to it.
>
If a ketone is produced after ozonolysis, at least one of the double bonded carbon atoms in the alkene must be disubstituted.
>
The total number of hydrogen and carbon atoms in the original alkene is equal to the total number of carbon and hydrogen atoms in two products formed in the ozonolysis reaction.

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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 8, Problem 60P

Interpretation Introduction

Interpretation:

The structure of sabinene and the other compound, which is formed in the ozonolysis of sabinene followed by hydrolysis in the presence of zinc, is to be given. Also, the structure of Δ3-carene, which gives compound B as a product of ozonolysis reaction, is to be given.

Concept introduction:
>
Ozonolysis of alkenes produces carbonyl compounds. These carbonyl compounds can be formaldehyde, other aldehydes, or ketones, depending upon the structure of the alkene used in the reaction.
>
On ozonolysis, cyclic alkenes produce a single compound containing two carbonyl groups.
>
If formaldehyde is produced after ozonolysis, the alkene has a terminal double bond.
>
If an aldehyde is produced after ozonolysis, at least one of the double bonded carbon atoms in the alkene has a hydrogen attached to it.
>
If a ketone is produced after ozonolysis, at least one of the double bonded carbon atoms in the alkene must be disubstituted.
>
The total number of hydrogen and carbon atoms in the original alkene is equal to the total number of carbon and hydrogen atoms in two products formed in the ozonolysis reaction.

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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 8, Problem 60P

Interpretation Introduction