(a) Interpretation: The structure from the provided IUPAC name is to be drawn. Concept introduction: If a molecule contains at least one ring entirely made up of carbon and hydrogen atoms, then such a ring could establish the root as a ‘cycloalkane’. Alternatively, the ring could serve as a substituent and called cycloalkyl groups. Whether a ring is treated as a root or a substituent depends on the relative number of carbon atoms in it. If the largest carbon ring has as many or more carbons than the longest continuous straight carbon chain, then the ring serves as the parent. If the longest continuous carbon chain has more carbon atoms than the longest continuous straight carbon chain, then the longest continuous straight chain serves as a parent and ring serves as a substituent. When the parent is a cycloalkane, then C1 has the greatest number of attached substituents, and numbering increases clockwise or anticlockwise around the ring so that the next substituent is encountered the earliest. Prefixes are used to indicate the number of substituents attached to the ring or to the longest continuous straight chain.

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Answer 1

Question

Chapter A, Problem A.27P

Interpretation Introduction

(a)

Interpretation:

The structure from the provided IUPAC name is to be drawn.

Concept introduction:

If a molecule contains at least one ring entirely made up of carbon and hydrogen atoms, then such a ring could establish the root as a ‘cycloalkane’. Alternatively, the ring could serve as a substituent and called cycloalkyl groups. Whether a ring is treated as a root or a substituent depends on the relative number of carbon atoms in it. If the largest carbon ring has as many or more carbons than the longest continuous straight carbon chain, then the ring serves as the parent. If the longest continuous carbon chain has more carbon atoms than the longest continuous straight carbon chain, then the longest continuous straight chain serves as a parent and ring serves as a substituent. When the parent is a cycloalkane, then C1 has the greatest number of attached substituents, and numbering increases clockwise or anticlockwise around the ring so that the next substituent is encountered the earliest. Prefixes are used to indicate the number of substituents attached to the ring or to the longest continuous straight chain.

Interpretation Introduction

(b)

Interpretation:

The structure from the given IUPAC name is to be drawn.

Concept introduction:

Interpretation Introduction

(c)

Interpretation:

The structure from the provided IUPAC name is to be drawn.

Concept introduction:

If a molecule contains at least one ring entirely made up of carbon and hydrogen atoms, then such a ring could establish the root as a ‘cycloalkane’. Alternatively, the ring could serve as a substituent and called cycloalkyl groups. Whether a ring is treated as a root or a substituent depends on the relative number of carbon atoms in it. If the largest carbon ring has as many or more carbons than the longest continuous straight carbon chain, then the ring serves as the parent. If the longest continuous carbon chain has more carbon atoms than the longest continuous straight carbon chain, then the longest continuous straight chain serves as a parent and ring serves as a substituent. When the parent is a cycloalkane, then C1 has the greatest number of attached substituents, and numbering increases clockwise or anticlockwise around the ring so that the next substituent is encountered the earliest. Prefixes are used to indicate the number of substituents attached to the ring or to the longest continuous straight chain.

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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 A, Problem A.27P

Interpretation Introduction

(a)

Interpretation:

The structure from the provided IUPAC name is to be drawn.

Concept introduction:

If a molecule contains at least one ring entirely made up of carbon and hydrogen atoms, then such a ring could establish the root as a ‘cycloalkane’. Alternatively, the ring could serve as a substituent and called cycloalkyl groups. Whether a ring is treated as a root or a substituent depends on the relative number of carbon atoms in it. If the largest carbon ring has as many or more carbons than the longest continuous straight carbon chain, then the ring serves as the parent. If the longest continuous carbon chain has more carbon atoms than the longest continuous straight carbon chain, then the longest continuous straight chain serves as a parent and ring serves as a substituent. When the parent is a cycloalkane, then C1 has the greatest number of attached substituents, and numbering increases clockwise or anticlockwise around the ring so that the next substituent is encountered the earliest. Prefixes are used to indicate the number of substituents attached to the ring or to the longest continuous straight chain.

Interpretation Introduction

(b)

Interpretation:

The structure from the given IUPAC name is to be drawn.

Concept introduction:

Interpretation Introduction

(c)

Interpretation:

The structure from the provided IUPAC name is to be drawn.

Concept introduction:

If a molecule contains at least one ring entirely made up of carbon and hydrogen atoms, then such a ring could establish the root as a ‘cycloalkane’. Alternatively, the ring could serve as a substituent and called cycloalkyl groups. Whether a ring is treated as a root or a substituent depends on the relative number of carbon atoms in it. If the largest carbon ring has as many or more carbons than the longest continuous straight carbon chain, then the ring serves as the parent. If the longest continuous carbon chain has more carbon atoms than the longest continuous straight carbon chain, then the longest continuous straight chain serves as a parent and ring serves as a substituent. When the parent is a cycloalkane, then C1 has the greatest number of attached substituents, and numbering increases clockwise or anticlockwise around the ring so that the next substituent is encountered the earliest. Prefixes are used to indicate the number of substituents attached to the ring or to the longest continuous straight chain.

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Answer 3

Question

Chapter A, Problem A.27P

Interpretation Introduction

(a)

Interpretation:

The structure from the provided IUPAC name is to be drawn.

Concept introduction:

If a molecule contains at least one ring entirely made up of carbon and hydrogen atoms, then such a ring could establish the root as a ‘cycloalkane’. Alternatively, the ring could serve as a substituent and called cycloalkyl groups. Whether a ring is treated as a root or a substituent depends on the relative number of carbon atoms in it. If the largest carbon ring has as many or more carbons than the longest continuous straight carbon chain, then the ring serves as the parent. If the longest continuous carbon chain has more carbon atoms than the longest continuous straight carbon chain, then the longest continuous straight chain serves as a parent and ring serves as a substituent. When the parent is a cycloalkane, then C1 has the greatest number of attached substituents, and numbering increases clockwise or anticlockwise around the ring so that the next substituent is encountered the earliest. Prefixes are used to indicate the number of substituents attached to the ring or to the longest continuous straight chain.

Interpretation Introduction

(b)

Interpretation:

The structure from the given IUPAC name is to be drawn.

Concept introduction:

Interpretation Introduction

(c)

Interpretation:

The structure from the provided IUPAC name is to be drawn.

Concept introduction:

If a molecule contains at least one ring entirely made up of carbon and hydrogen atoms, then such a ring could establish the root as a ‘cycloalkane’. Alternatively, the ring could serve as a substituent and called cycloalkyl groups. Whether a ring is treated as a root or a substituent depends on the relative number of carbon atoms in it. If the largest carbon ring has as many or more carbons than the longest continuous straight carbon chain, then the ring serves as the parent. If the longest continuous carbon chain has more carbon atoms than the longest continuous straight carbon chain, then the longest continuous straight chain serves as a parent and ring serves as a substituent. When the parent is a cycloalkane, then C1 has the greatest number of attached substituents, and numbering increases clockwise or anticlockwise around the ring so that the next substituent is encountered the earliest. Prefixes are used to indicate the number of substituents attached to the ring or to the longest continuous straight chain.

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Answer 4

Question

Chapter A, Problem A.27P

Interpretation Introduction

(a)

Interpretation:

The structure from the provided IUPAC name is to be drawn.

Concept introduction:

If a molecule contains at least one ring entirely made up of carbon and hydrogen atoms, then such a ring could establish the root as a ‘cycloalkane’. Alternatively, the ring could serve as a substituent and called cycloalkyl groups. Whether a ring is treated as a root or a substituent depends on the relative number of carbon atoms in it. If the largest carbon ring has as many or more carbons than the longest continuous straight carbon chain, then the ring serves as the parent. If the longest continuous carbon chain has more carbon atoms than the longest continuous straight carbon chain, then the longest continuous straight chain serves as a parent and ring serves as a substituent. When the parent is a cycloalkane, then C1 has the greatest number of attached substituents, and numbering increases clockwise or anticlockwise around the ring so that the next substituent is encountered the earliest. Prefixes are used to indicate the number of substituents attached to the ring or to the longest continuous straight chain.

Interpretation Introduction

(b)

Interpretation:

The structure from the given IUPAC name is to be drawn.

Concept introduction:

Interpretation Introduction

(c)

Interpretation:

The structure from the provided IUPAC name is to be drawn.

Concept introduction:

If a molecule contains at least one ring entirely made up of carbon and hydrogen atoms, then such a ring could establish the root as a ‘cycloalkane’. Alternatively, the ring could serve as a substituent and called cycloalkyl groups. Whether a ring is treated as a root or a substituent depends on the relative number of carbon atoms in it. If the largest carbon ring has as many or more carbons than the longest continuous straight carbon chain, then the ring serves as the parent. If the longest continuous carbon chain has more carbon atoms than the longest continuous straight carbon chain, then the longest continuous straight chain serves as a parent and ring serves as a substituent. When the parent is a cycloalkane, then C1 has the greatest number of attached substituents, and numbering increases clockwise or anticlockwise around the ring so that the next substituent is encountered the earliest. Prefixes are used to indicate the number of substituents attached to the ring or to the longest continuous straight chain.

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Answer 5

Chapter A, Problem A.27P

Interpretation Introduction

(a)

Interpretation:

The structure from the provided IUPAC name is to be drawn.

Concept introduction:

If a molecule contains at least one ring entirely made up of carbon and hydrogen atoms, then such a ring could establish the root as a ‘cycloalkane’. Alternatively, the ring could serve as a substituent and called cycloalkyl groups. Whether a ring is treated as a root or a substituent depends on the relative number of carbon atoms in it. If the largest carbon ring has as many or more carbons than the longest continuous straight carbon chain, then the ring serves as the parent. If the longest continuous carbon chain has more carbon atoms than the longest continuous straight carbon chain, then the longest continuous straight chain serves as a parent and ring serves as a substituent. When the parent is a cycloalkane, then C1 has the greatest number of attached substituents, and numbering increases clockwise or anticlockwise around the ring so that the next substituent is encountered the earliest. Prefixes are used to indicate the number of substituents attached to the ring or to the longest continuous straight chain.

Interpretation Introduction

(b)

Interpretation:

The structure from the given IUPAC name is to be drawn.

Concept introduction:

Interpretation Introduction

(c)

Interpretation:

The structure from the provided IUPAC name is to be drawn.

Concept introduction:

If a molecule contains at least one ring entirely made up of carbon and hydrogen atoms, then such a ring could establish the root as a ‘cycloalkane’. Alternatively, the ring could serve as a substituent and called cycloalkyl groups. Whether a ring is treated as a root or a substituent depends on the relative number of carbon atoms in it. If the largest carbon ring has as many or more carbons than the longest continuous straight carbon chain, then the ring serves as the parent. If the longest continuous carbon chain has more carbon atoms than the longest continuous straight carbon chain, then the longest continuous straight chain serves as a parent and ring serves as a substituent. When the parent is a cycloalkane, then C1 has the greatest number of attached substituents, and numbering increases clockwise or anticlockwise around the ring so that the next substituent is encountered the earliest. Prefixes are used to indicate the number of substituents attached to the ring or to the longest continuous straight chain.

Answer 6

Chapter A, Problem A.27P

Interpretation Introduction

(a)

Interpretation:

The structure from the provided IUPAC name is to be drawn.

Concept introduction:

If a molecule contains at least one ring entirely made up of carbon and hydrogen atoms, then such a ring could establish the root as a ‘cycloalkane’. Alternatively, the ring could serve as a substituent and called cycloalkyl groups. Whether a ring is treated as a root or a substituent depends on the relative number of carbon atoms in it. If the largest carbon ring has as many or more carbons than the longest continuous straight carbon chain, then the ring serves as the parent. If the longest continuous carbon chain has more carbon atoms than the longest continuous straight carbon chain, then the longest continuous straight chain serves as a parent and ring serves as a substituent. When the parent is a cycloalkane, then C1 has the greatest number of attached substituents, and numbering increases clockwise or anticlockwise around the ring so that the next substituent is encountered the earliest. Prefixes are used to indicate the number of substituents attached to the ring or to the longest continuous straight chain.

Answer 7

Chapter A, Problem A.27P

Interpretation Introduction

(a)

Interpretation:

The structure from the provided IUPAC name is to be drawn.

Concept introduction:

If a molecule contains at least one ring entirely made up of carbon and hydrogen atoms, then such a ring could establish the root as a ‘cycloalkane’. Alternatively, the ring could serve as a substituent and called cycloalkyl groups. Whether a ring is treated as a root or a substituent depends on the relative number of carbon atoms in it. If the largest carbon ring has as many or more carbons than the longest continuous straight carbon chain, then the ring serves as the parent. If the longest continuous carbon chain has more carbon atoms than the longest continuous straight carbon chain, then the longest continuous straight chain serves as a parent and ring serves as a substituent. When the parent is a cycloalkane, then C1 has the greatest number of attached substituents, and numbering increases clockwise or anticlockwise around the ring so that the next substituent is encountered the earliest. Prefixes are used to indicate the number of substituents attached to the ring or to the longest continuous straight chain.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The structure from the given IUPAC name is to be drawn.

Concept introduction:

Answer 9

Interpretation Introduction

(b)

Interpretation:

The structure from the given IUPAC name is to be drawn.

Concept introduction:

Answer 10

Interpretation Introduction

(c)

Interpretation:

The structure from the provided IUPAC name is to be drawn.

Concept introduction:

If a molecule contains at least one ring entirely made up of carbon and hydrogen atoms, then such a ring could establish the root as a ‘cycloalkane’. Alternatively, the ring could serve as a substituent and called cycloalkyl groups. Whether a ring is treated as a root or a substituent depends on the relative number of carbon atoms in it. If the largest carbon ring has as many or more carbons than the longest continuous straight carbon chain, then the ring serves as the parent. If the longest continuous carbon chain has more carbon atoms than the longest continuous straight carbon chain, then the longest continuous straight chain serves as a parent and ring serves as a substituent. When the parent is a cycloalkane, then C1 has the greatest number of attached substituents, and numbering increases clockwise or anticlockwise around the ring so that the next substituent is encountered the earliest. Prefixes are used to indicate the number of substituents attached to the ring or to the longest continuous straight chain.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The structure from the provided IUPAC name is to be drawn.

Concept introduction:

If a molecule contains at least one ring entirely made up of carbon and hydrogen atoms, then such a ring could establish the root as a ‘cycloalkane’. Alternatively, the ring could serve as a substituent and called cycloalkyl groups. Whether a ring is treated as a root or a substituent depends on the relative number of carbon atoms in it. If the largest carbon ring has as many or more carbons than the longest continuous straight carbon chain, then the ring serves as the parent. If the longest continuous carbon chain has more carbon atoms than the longest continuous straight carbon chain, then the longest continuous straight chain serves as a parent and ring serves as a substituent. When the parent is a cycloalkane, then C1 has the greatest number of attached substituents, and numbering increases clockwise or anticlockwise around the ring so that the next substituent is encountered the earliest. Prefixes are used to indicate the number of substituents attached to the ring or to the longest continuous straight chain.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. A - Prob. A.1P Ch. A - Prob. A.2P Ch. A - Prob. A.3P Ch. A - Prob. A.4P Ch. A - Prob. A.5P Ch. A - Prob. A.6P Ch. A - Prob. A.7P Ch. A - Prob. A.8P Ch. A - Prob. A.9P Ch. A - Prob. A.10P

Solution Summary: The structure for the given IUPAC name is as shown in Figure 1 above.

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(b)

Interpretation:

The structure from the given IUPAC name is to be drawn.

Concept introduction:

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Chapter A Solutions

Solution Summary: The structure for the given IUPAC name is as shown in Figure 1 above.

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(b) Interpretation: The structure from the given IUPAC name is to be drawn. Concept introduction:

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Chapter A Solutions

(b)

Interpretation:

The structure from the given IUPAC name is to be drawn.

Concept introduction: