Correct IUPAC name for the given ketone has to be assigned. Concept Introduction: For naming a ketone in IUPAC nomenclature , the suffix “-one” is added to the parent alkane name. IUPAC rules for naming a ketone: • The longest parent carbon chain is identified that includes the carbonyl group. • The parent chain name is changed by replacing the suffix “-e” with “-one”. • Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name. • The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name. • Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

Question

16. The proton NMR spectral information shown in this problem is for a compound with formula CioH,N. Expansions are shown for the region from 8.7 to 7.0 ppm. The normal carbon-13 spec- tral results, including DEPT-135 and DEPT-90 results, are tabulated: 7 J Normal Carbon DEPT-135 DEPT-90 19 ppm Positive No peak 122 Positive Positive cus и 124 Positive Positive 126 Positive Positive 128 No peak No peak 4° 129 Positive Positive 130 Positive Positive (144 No peak No peak 148 No peak No peak 150 Positive Positive してし

Answer 1

Question

Chapter 15, Problem 15.40EP

(a)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

(b)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

(c)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

(d)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

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16. The proton NMR spectral information shown in this problem is for a compound with formula CioH,N. Expansions are shown for the region from 8.7 to 7.0 ppm. The normal carbon-13 spec- tral results, including DEPT-135 and DEPT-90 results, are tabulated: 7 J Normal Carbon DEPT-135 DEPT-90 19 ppm Positive No peak 122 Positive Positive cus и 124 Positive Positive 126 Positive Positive 128 No peak No peak 4° 129 Positive Positive 130 Positive Positive (144 No peak No peak 148 No peak No peak 150 Positive Positive してし

3. Propose a synthesis for the following transformation. Do not draw an arrow-pushing mechanism below, but make sure to draw the product of each proposed step (3 points). + En CN CN

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Answer 2

Question

Chapter 15, Problem 15.40EP

(a)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

(b)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

(c)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

(d)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

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Answer 3

Question

Chapter 15, Problem 15.40EP

(a)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

(b)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

(c)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

(d)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

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Answer 4

Question

Chapter 15, Problem 15.40EP

(a)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

(b)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

(c)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

(d)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

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Answer 5

Chapter 15, Problem 15.40EP

(a)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

(b)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

(c)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

(d)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

Answer 6

Chapter 15, Problem 15.40EP

(a)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

Answer 7

Chapter 15, Problem 15.40EP

(a)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

Answer 8

(b)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

Answer 9

(b)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

Answer 10

(c)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

Answer 11

(c)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

Answer 12

(d)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

Answer 13

(d)

Interpretation Introduction

Interpretation:

Correct IUPAC name for the given ketone has to be assigned.

Concept Introduction:

For naming a ketone in IUPAC nomenclature, the suffix “-one” is added to the parent alkane name.

IUPAC rules for naming a ketone:

• The longest parent carbon chain is identified that includes the carbonyl group.

• The parent chain name is changed by replacing the suffix “-e” with “-one”.

• Numbering is done in a way that the carbonyl group gets the least numbering. The position of the carbonyl group is indicated in the name.

• The identity and location of substituents if any has to be determined and this information has to be added in front of the IUPAC name.

• Cyclic ketones are named by adding the suffix “-one” to the name of the carbon ring. The substituents are numbered so that it gets the least numbering starting from the carbonyl group that is given the number 1.

Answer 14

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Answer 25

Ch. 15.1 - Prob. 1QQ Ch. 15.1 - Prob. 2QQ Ch. 15.2 - Prob. 1QQ Ch. 15.2 - Prob. 2QQ Ch. 15.2 - Prob. 3QQ Ch. 15.3 - Prob. 1QQ Ch. 15.3 - Prob. 2QQ Ch. 15.3 - Prob. 3QQ Ch. 15.4 - Prob. 1QQ Ch. 15.4 - Prob. 2QQ

Solution Summary: The author explains the IUPAC rules for naming a ketone: the longest parent carbon chain is identified and the carbonyl group gets the least numbering.

Chapter 15 Solutions