The IUPAC name of the given compound and the products of the given reaction to be predicted Concept Introduction: IUPAC naming nomenclature: Name the parent compound: Find the longest chain containing the double bond or triple bond and add the suffix ‘-ene’ or ‘-yne’ to the end of the main chain name. Number the carbon atoms in the main chain so that those with multiple bonds have the lowest index numbers possible: Write the full name: List the substituents in alphabetical order. Use commas to separate the numbers and the hyphen to separate number from words. Indicate the position of double or triple bond in chain by giving the number of the first multiple-bond carbon. Addition reaction: A general reaction type in which a substance X-Y adds to the multiple bond of an unsaturated reactant to yield a saturated product that has only single bonds. Hydrohalogenation (Addition of hydrogen halide to alkenes ): The addition of hydrogen halide to a multiple bond to give an alkyl halide product. Hydration: The Addition of water to a multiple bond to give an alcohol product. An alkene does not react with pure water alone; it requires a small amount of acid to catalyst the reaction. Alkene isomerization: The location of double bond is changed in the reaction process. Markovnikov’s rule: In the addition of HX to an alkene, the major product arises as the nucleophile attached to the less substituent carbon centre and hydrogen attached to the more substituent carbon centre.

Question

Want to see more full solutions like this?

Answer 1

Question

Chapter 13, Problem 13.24UKC

(a)

Interpretation Introduction

Interpretation:

The IUPAC name of the given compound and the products of the given reaction to be predicted

Concept Introduction:

IUPAC naming nomenclature:

Name the parent compound: Find the longest chain containing the double bond or triple bond and add the suffix ‘-ene’ or ‘-yne’ to the end of the main chain name.

Number the carbon atoms in the main chain so that those with multiple bonds have the lowest index numbers possible:

Write the full name: List the substituents in alphabetical order. Use commas to separate the numbers and the hyphen to separate number from words. Indicate the position of double or triple bond in chain by giving the number of the first multiple-bond carbon.

Addition reaction: A general reaction type in which a substance X-Y adds to the multiple bond of an unsaturated reactant to yield a saturated product that has only single bonds.

Hydrohalogenation (Addition of hydrogen halide to alkenes): The addition of hydrogen halide to a multiple bond to give an alkyl halide product.

Hydration: The Addition of water to a multiple bond to give an alcohol product. An alkene does not react with pure water alone; it requires a small amount of acid to catalyst the reaction.

Alkene isomerization: The location of double bond is changed in the reaction process.

Markovnikov’s rule: In the addition of $HX$ to an alkene, the major product arises as the nucleophile attached to the less substituent carbon centre and hydrogen attached to the more substituent carbon centre.

(a)

Expert Solution

Answer to Problem 13.24UKC

The IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

The products obtained respectively are,

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 1

Explanation of Solution

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 2

In the given compound, the parent chain has seven carbons with the double bond between $C-2$ and C-3. The numbering done in the priority order, in which the substituents gets the lowest possible number. The parent name is 2-heptene. Include the substituents in the IUPAC name with the lowest possible number. The methyl group is located at both second and fifth carbon.

Therefore, the IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

Hydrohalogenation reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 3

In the given above reaction, the addition of $HBr$ across the double bond gives rise to the formation of carbocation, the tertiary carbocation is highly stable than the secondary carbocation and the nucleophilic attack of bromide ion at the carbocation centre leads to the product formation. In the product, the hydrogen attached at the less substituted carbon centre and thus the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Hydration reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 4

The addition of water molecule across the double bond requires small amount of acid to catalyse the reaction. In the given above reaction, the addition of acidic proton across the double bond gives rise to the formation of carbocation, the tertiary carbocation is highly stable and the nucleophilic attack of water molecule at the carbocation centre leads to the product formation followed by deprotonation. In the product, the hydrogen attached at the less substituted carbon centre and the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Acid-catalysed reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 5

The reaction of alkene with acid (as catalyst) indicates no other reagent is present. The protonation of alkene forms the tertiary carbocation intermediate. The deprotonation that occur in the intermediate leads to the di-substituted alkene. The reaction is an alkene isomerization.

(b)

Interpretation Introduction

Interpretation:

The IUPAC name of the given compound and the products of the given reaction to be predicted

Concept Introduction:

IUPAC naming nomenclature:

Name the parent compound: Find the longest chain containing the double bond or triple bond and add the suffix ‘-ene’ or ‘-yne’ to the end of the main chain name.

Number the carbon atoms in the main chain so that those with multiple bonds have the lowest index numbers possible:

Write the full name: List the substituents in alphabetical order. Use commas to separate the numbers and the hyphen to separate number from words. Indicate the position of double or triple bond in chain by giving the number of the first multiple-bond carbon.

Addition reaction: A general reaction type in which a substance X-Y adds to the multiple bond of an unsaturated reactant to yield a saturated product that has only single bonds.

Hydrohalogenation (Addition of hydrogen halide to alkenes): The addition of hydrogen halide to a multiple bond to give an alkyl halide product.

Hydration: The Addition of water to a multiple bond to give an alcohol product. An alkene does not react with pure water alone; it requires a small amount of acid to catalyst the reaction.

Alkene isomerization: The location of double bond is changed in the reaction process.

Markovnikov’s rule: In the addition of $HX$ to an alkene, the major product arises as the nucleophile attached to the less substituent carbon centre and hydrogen attached to the more substituent carbon centre.

(b)

Expert Solution

Answer to Problem 13.24UKC

The IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

The products obtained respectively are,

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 6

Explanation of Solution

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 7

In the given compound, the parent chain has five carbons with the double bond between C-1 and C-2. The numbering done in the priority order, in which the substituents gets the lowest possible number. The parent name is 1-cyclopentene. Include the substituents in the IUPAC name with the lowest possible number. Two methyl groups are located at third carbon.

Therefore, the IUPAC name of the compound is 3,3-Dimethyl-1-cyclopentene.

Hydrohalogenation reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 8

In the given above reaction, the addition of $HBr$ across the double bond gives rise to the formation of carbocation, the secondary carbocation; the methyl shift occurred which leads to stable tertiary carbocation and the nucleophilic attack of bromide ion at the carbocation centre leads to the product formation. In the product, the hydrogen attached at the less substituted carbon centre and thus the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Hydration reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 9

The addition of water molecule across the double bond requires small amount of acid to catalyse the reaction. In the given above reaction, the addition of acidic proton across the double bond gives rise to the formation of carbocation; the methyl shift occurred which leads to stable tertiary carbocation and the nucleophilic attack of water molecule at the carbocation centre leads to the product formation followed by deprotonation. In the product, the hydrogen attached at the less substituted carbon centre and the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Acid-catalysed reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 10

The reaction of alkene with acid (as catalyst) indicates no other reagent is present. The protonation of alkene forms the secondary carbocation intermediate; the methyl shift occurred which leads to stable tertiary carbocation. The deprotonation that occur in the intermediate leads to the tetra-substituted alkene. The reaction is an alkene isomerization.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Students have asked these similar questions

I am a Biochemistry student and I am confused on how to analyze FRAP Analysis using Excel Spread Sheets. The following spread sheet has my 0 minute data listed at top and the 4 minute data listed on the bottom. Sheet: https://mnscu-my.sharepoint.com/:x:/g/personal/vi2163ss_go_minnstate_edu/EXjrCizWiXRPmpittqZA12IB8EkB5eE8iaRqj_iun-IAtg?rtime=Wo9zPHFY3Ug The formula for FRAP Analysis is: FRAP value = A (4 min sample) - A (0 min sample) over A (4 min 30 uM ascorbic acid) - A (0 min 30 uM ascorbic acid) multiplied by 30 uM and the dilution factor of 1/10

HO Fill in the missing boxes. ON 800 NO NO Glucose ATP NADH Hexokinase 1,3-Bisphosphoglycerate Mg2+ ADP NAD+, Pi Phosphoglucose Isomerase Glucose-6-Phosphate ON 沁 Glyceraldehyde-3-Phosphate HO حلمة ADP ADP Phospho Mg2+ glycerate Dihydroxyacetone Phosphate ATP kinase ATP Phosphoglycerate 3-phosphoglycerate Mutase H₁₂O Fructose-6-Phosphate ATP Mg2+ ADP Fructose-1,6-Bisphosphate 2-phosphoglycerate H₂O Phosphoenolpyruvate ADP Mg2+ ATP Pyruvate

In a diffraction experiment of a native crystal, intensity of reflection (-1 0 6) is equivalent to the intensity of reflection (1 0 -6). true or false?

Answer 2

Question

Chapter 13, Problem 13.24UKC

(a)

Interpretation Introduction

Interpretation:

The IUPAC name of the given compound and the products of the given reaction to be predicted

Concept Introduction:

IUPAC naming nomenclature:

Name the parent compound: Find the longest chain containing the double bond or triple bond and add the suffix ‘-ene’ or ‘-yne’ to the end of the main chain name.

Number the carbon atoms in the main chain so that those with multiple bonds have the lowest index numbers possible:

Write the full name: List the substituents in alphabetical order. Use commas to separate the numbers and the hyphen to separate number from words. Indicate the position of double or triple bond in chain by giving the number of the first multiple-bond carbon.

Addition reaction: A general reaction type in which a substance X-Y adds to the multiple bond of an unsaturated reactant to yield a saturated product that has only single bonds.

Hydrohalogenation (Addition of hydrogen halide to alkenes): The addition of hydrogen halide to a multiple bond to give an alkyl halide product.

Hydration: The Addition of water to a multiple bond to give an alcohol product. An alkene does not react with pure water alone; it requires a small amount of acid to catalyst the reaction.

Alkene isomerization: The location of double bond is changed in the reaction process.

Markovnikov’s rule: In the addition of $HX$ to an alkene, the major product arises as the nucleophile attached to the less substituent carbon centre and hydrogen attached to the more substituent carbon centre.

(a)

Expert Solution

Answer to Problem 13.24UKC

The IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

The products obtained respectively are,

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 1

Explanation of Solution

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 2

In the given compound, the parent chain has seven carbons with the double bond between $C-2$ and C-3. The numbering done in the priority order, in which the substituents gets the lowest possible number. The parent name is 2-heptene. Include the substituents in the IUPAC name with the lowest possible number. The methyl group is located at both second and fifth carbon.

Therefore, the IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

Hydrohalogenation reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 3

In the given above reaction, the addition of $HBr$ across the double bond gives rise to the formation of carbocation, the tertiary carbocation is highly stable than the secondary carbocation and the nucleophilic attack of bromide ion at the carbocation centre leads to the product formation. In the product, the hydrogen attached at the less substituted carbon centre and thus the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Hydration reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 4

The addition of water molecule across the double bond requires small amount of acid to catalyse the reaction. In the given above reaction, the addition of acidic proton across the double bond gives rise to the formation of carbocation, the tertiary carbocation is highly stable and the nucleophilic attack of water molecule at the carbocation centre leads to the product formation followed by deprotonation. In the product, the hydrogen attached at the less substituted carbon centre and the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Acid-catalysed reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 5

The reaction of alkene with acid (as catalyst) indicates no other reagent is present. The protonation of alkene forms the tertiary carbocation intermediate. The deprotonation that occur in the intermediate leads to the di-substituted alkene. The reaction is an alkene isomerization.

(b)

Interpretation Introduction

Interpretation:

The IUPAC name of the given compound and the products of the given reaction to be predicted

Concept Introduction:

IUPAC naming nomenclature:

Name the parent compound: Find the longest chain containing the double bond or triple bond and add the suffix ‘-ene’ or ‘-yne’ to the end of the main chain name.

Number the carbon atoms in the main chain so that those with multiple bonds have the lowest index numbers possible:

Write the full name: List the substituents in alphabetical order. Use commas to separate the numbers and the hyphen to separate number from words. Indicate the position of double or triple bond in chain by giving the number of the first multiple-bond carbon.

Addition reaction: A general reaction type in which a substance X-Y adds to the multiple bond of an unsaturated reactant to yield a saturated product that has only single bonds.

Hydrohalogenation (Addition of hydrogen halide to alkenes): The addition of hydrogen halide to a multiple bond to give an alkyl halide product.

Hydration: The Addition of water to a multiple bond to give an alcohol product. An alkene does not react with pure water alone; it requires a small amount of acid to catalyst the reaction.

Alkene isomerization: The location of double bond is changed in the reaction process.

Markovnikov’s rule: In the addition of $HX$ to an alkene, the major product arises as the nucleophile attached to the less substituent carbon centre and hydrogen attached to the more substituent carbon centre.

(b)

Expert Solution

Answer to Problem 13.24UKC

The IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

The products obtained respectively are,

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 6

Explanation of Solution

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 7

In the given compound, the parent chain has five carbons with the double bond between C-1 and C-2. The numbering done in the priority order, in which the substituents gets the lowest possible number. The parent name is 1-cyclopentene. Include the substituents in the IUPAC name with the lowest possible number. Two methyl groups are located at third carbon.

Therefore, the IUPAC name of the compound is 3,3-Dimethyl-1-cyclopentene.

Hydrohalogenation reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 8

In the given above reaction, the addition of $HBr$ across the double bond gives rise to the formation of carbocation, the secondary carbocation; the methyl shift occurred which leads to stable tertiary carbocation and the nucleophilic attack of bromide ion at the carbocation centre leads to the product formation. In the product, the hydrogen attached at the less substituted carbon centre and thus the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Hydration reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 9

The addition of water molecule across the double bond requires small amount of acid to catalyse the reaction. In the given above reaction, the addition of acidic proton across the double bond gives rise to the formation of carbocation; the methyl shift occurred which leads to stable tertiary carbocation and the nucleophilic attack of water molecule at the carbocation centre leads to the product formation followed by deprotonation. In the product, the hydrogen attached at the less substituted carbon centre and the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Acid-catalysed reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 10

The reaction of alkene with acid (as catalyst) indicates no other reagent is present. The protonation of alkene forms the secondary carbocation intermediate; the methyl shift occurred which leads to stable tertiary carbocation. The deprotonation that occur in the intermediate leads to the tetra-substituted alkene. The reaction is an alkene isomerization.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 3

Question

Chapter 13, Problem 13.24UKC

(a)

Interpretation Introduction

Interpretation:

The IUPAC name of the given compound and the products of the given reaction to be predicted

Concept Introduction:

IUPAC naming nomenclature:

Name the parent compound: Find the longest chain containing the double bond or triple bond and add the suffix ‘-ene’ or ‘-yne’ to the end of the main chain name.

Number the carbon atoms in the main chain so that those with multiple bonds have the lowest index numbers possible:

Write the full name: List the substituents in alphabetical order. Use commas to separate the numbers and the hyphen to separate number from words. Indicate the position of double or triple bond in chain by giving the number of the first multiple-bond carbon.

Addition reaction: A general reaction type in which a substance X-Y adds to the multiple bond of an unsaturated reactant to yield a saturated product that has only single bonds.

Hydrohalogenation (Addition of hydrogen halide to alkenes): The addition of hydrogen halide to a multiple bond to give an alkyl halide product.

Hydration: The Addition of water to a multiple bond to give an alcohol product. An alkene does not react with pure water alone; it requires a small amount of acid to catalyst the reaction.

Alkene isomerization: The location of double bond is changed in the reaction process.

Markovnikov’s rule: In the addition of $HX$ to an alkene, the major product arises as the nucleophile attached to the less substituent carbon centre and hydrogen attached to the more substituent carbon centre.

(a)

Expert Solution

Answer to Problem 13.24UKC

The IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

The products obtained respectively are,

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 1

Explanation of Solution

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 2

In the given compound, the parent chain has seven carbons with the double bond between $C-2$ and C-3. The numbering done in the priority order, in which the substituents gets the lowest possible number. The parent name is 2-heptene. Include the substituents in the IUPAC name with the lowest possible number. The methyl group is located at both second and fifth carbon.

Therefore, the IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

Hydrohalogenation reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 3

In the given above reaction, the addition of $HBr$ across the double bond gives rise to the formation of carbocation, the tertiary carbocation is highly stable than the secondary carbocation and the nucleophilic attack of bromide ion at the carbocation centre leads to the product formation. In the product, the hydrogen attached at the less substituted carbon centre and thus the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Hydration reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 4

The addition of water molecule across the double bond requires small amount of acid to catalyse the reaction. In the given above reaction, the addition of acidic proton across the double bond gives rise to the formation of carbocation, the tertiary carbocation is highly stable and the nucleophilic attack of water molecule at the carbocation centre leads to the product formation followed by deprotonation. In the product, the hydrogen attached at the less substituted carbon centre and the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Acid-catalysed reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 5

The reaction of alkene with acid (as catalyst) indicates no other reagent is present. The protonation of alkene forms the tertiary carbocation intermediate. The deprotonation that occur in the intermediate leads to the di-substituted alkene. The reaction is an alkene isomerization.

(b)

Interpretation Introduction

Interpretation:

The IUPAC name of the given compound and the products of the given reaction to be predicted

Concept Introduction:

IUPAC naming nomenclature:

Name the parent compound: Find the longest chain containing the double bond or triple bond and add the suffix ‘-ene’ or ‘-yne’ to the end of the main chain name.

Number the carbon atoms in the main chain so that those with multiple bonds have the lowest index numbers possible:

Write the full name: List the substituents in alphabetical order. Use commas to separate the numbers and the hyphen to separate number from words. Indicate the position of double or triple bond in chain by giving the number of the first multiple-bond carbon.

Addition reaction: A general reaction type in which a substance X-Y adds to the multiple bond of an unsaturated reactant to yield a saturated product that has only single bonds.

Hydrohalogenation (Addition of hydrogen halide to alkenes): The addition of hydrogen halide to a multiple bond to give an alkyl halide product.

Hydration: The Addition of water to a multiple bond to give an alcohol product. An alkene does not react with pure water alone; it requires a small amount of acid to catalyst the reaction.

Alkene isomerization: The location of double bond is changed in the reaction process.

Markovnikov’s rule: In the addition of $HX$ to an alkene, the major product arises as the nucleophile attached to the less substituent carbon centre and hydrogen attached to the more substituent carbon centre.

(b)

Expert Solution

Answer to Problem 13.24UKC

The IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

The products obtained respectively are,

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 6

Explanation of Solution

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 7

In the given compound, the parent chain has five carbons with the double bond between C-1 and C-2. The numbering done in the priority order, in which the substituents gets the lowest possible number. The parent name is 1-cyclopentene. Include the substituents in the IUPAC name with the lowest possible number. Two methyl groups are located at third carbon.

Therefore, the IUPAC name of the compound is 3,3-Dimethyl-1-cyclopentene.

Hydrohalogenation reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 8

In the given above reaction, the addition of $HBr$ across the double bond gives rise to the formation of carbocation, the secondary carbocation; the methyl shift occurred which leads to stable tertiary carbocation and the nucleophilic attack of bromide ion at the carbocation centre leads to the product formation. In the product, the hydrogen attached at the less substituted carbon centre and thus the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Hydration reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 9

The addition of water molecule across the double bond requires small amount of acid to catalyse the reaction. In the given above reaction, the addition of acidic proton across the double bond gives rise to the formation of carbocation; the methyl shift occurred which leads to stable tertiary carbocation and the nucleophilic attack of water molecule at the carbocation centre leads to the product formation followed by deprotonation. In the product, the hydrogen attached at the less substituted carbon centre and the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Acid-catalysed reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 10

The reaction of alkene with acid (as catalyst) indicates no other reagent is present. The protonation of alkene forms the secondary carbocation intermediate; the methyl shift occurred which leads to stable tertiary carbocation. The deprotonation that occur in the intermediate leads to the tetra-substituted alkene. The reaction is an alkene isomerization.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 4

Question

Chapter 13, Problem 13.24UKC

(a)

Interpretation Introduction

Interpretation:

The IUPAC name of the given compound and the products of the given reaction to be predicted

Concept Introduction:

IUPAC naming nomenclature:

Name the parent compound: Find the longest chain containing the double bond or triple bond and add the suffix ‘-ene’ or ‘-yne’ to the end of the main chain name.

Number the carbon atoms in the main chain so that those with multiple bonds have the lowest index numbers possible:

Write the full name: List the substituents in alphabetical order. Use commas to separate the numbers and the hyphen to separate number from words. Indicate the position of double or triple bond in chain by giving the number of the first multiple-bond carbon.

Addition reaction: A general reaction type in which a substance X-Y adds to the multiple bond of an unsaturated reactant to yield a saturated product that has only single bonds.

Hydrohalogenation (Addition of hydrogen halide to alkenes): The addition of hydrogen halide to a multiple bond to give an alkyl halide product.

Hydration: The Addition of water to a multiple bond to give an alcohol product. An alkene does not react with pure water alone; it requires a small amount of acid to catalyst the reaction.

Alkene isomerization: The location of double bond is changed in the reaction process.

Markovnikov’s rule: In the addition of $HX$ to an alkene, the major product arises as the nucleophile attached to the less substituent carbon centre and hydrogen attached to the more substituent carbon centre.

(a)

Expert Solution

Answer to Problem 13.24UKC

The IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

The products obtained respectively are,

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 1

Explanation of Solution

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 2

In the given compound, the parent chain has seven carbons with the double bond between $C-2$ and C-3. The numbering done in the priority order, in which the substituents gets the lowest possible number. The parent name is 2-heptene. Include the substituents in the IUPAC name with the lowest possible number. The methyl group is located at both second and fifth carbon.

Therefore, the IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

Hydrohalogenation reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 3

In the given above reaction, the addition of $HBr$ across the double bond gives rise to the formation of carbocation, the tertiary carbocation is highly stable than the secondary carbocation and the nucleophilic attack of bromide ion at the carbocation centre leads to the product formation. In the product, the hydrogen attached at the less substituted carbon centre and thus the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Hydration reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 4

The addition of water molecule across the double bond requires small amount of acid to catalyse the reaction. In the given above reaction, the addition of acidic proton across the double bond gives rise to the formation of carbocation, the tertiary carbocation is highly stable and the nucleophilic attack of water molecule at the carbocation centre leads to the product formation followed by deprotonation. In the product, the hydrogen attached at the less substituted carbon centre and the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Acid-catalysed reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 5

The reaction of alkene with acid (as catalyst) indicates no other reagent is present. The protonation of alkene forms the tertiary carbocation intermediate. The deprotonation that occur in the intermediate leads to the di-substituted alkene. The reaction is an alkene isomerization.

(b)

Interpretation Introduction

Interpretation:

The IUPAC name of the given compound and the products of the given reaction to be predicted

Concept Introduction:

IUPAC naming nomenclature:

Name the parent compound: Find the longest chain containing the double bond or triple bond and add the suffix ‘-ene’ or ‘-yne’ to the end of the main chain name.

Number the carbon atoms in the main chain so that those with multiple bonds have the lowest index numbers possible:

Write the full name: List the substituents in alphabetical order. Use commas to separate the numbers and the hyphen to separate number from words. Indicate the position of double or triple bond in chain by giving the number of the first multiple-bond carbon.

Addition reaction: A general reaction type in which a substance X-Y adds to the multiple bond of an unsaturated reactant to yield a saturated product that has only single bonds.

Hydrohalogenation (Addition of hydrogen halide to alkenes): The addition of hydrogen halide to a multiple bond to give an alkyl halide product.

Hydration: The Addition of water to a multiple bond to give an alcohol product. An alkene does not react with pure water alone; it requires a small amount of acid to catalyst the reaction.

Alkene isomerization: The location of double bond is changed in the reaction process.

Markovnikov’s rule: In the addition of $HX$ to an alkene, the major product arises as the nucleophile attached to the less substituent carbon centre and hydrogen attached to the more substituent carbon centre.

(b)

Expert Solution

Answer to Problem 13.24UKC

The IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

The products obtained respectively are,

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 6

Explanation of Solution

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 7

In the given compound, the parent chain has five carbons with the double bond between C-1 and C-2. The numbering done in the priority order, in which the substituents gets the lowest possible number. The parent name is 1-cyclopentene. Include the substituents in the IUPAC name with the lowest possible number. Two methyl groups are located at third carbon.

Therefore, the IUPAC name of the compound is 3,3-Dimethyl-1-cyclopentene.

Hydrohalogenation reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 8

In the given above reaction, the addition of $HBr$ across the double bond gives rise to the formation of carbocation, the secondary carbocation; the methyl shift occurred which leads to stable tertiary carbocation and the nucleophilic attack of bromide ion at the carbocation centre leads to the product formation. In the product, the hydrogen attached at the less substituted carbon centre and thus the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Hydration reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 9

The addition of water molecule across the double bond requires small amount of acid to catalyse the reaction. In the given above reaction, the addition of acidic proton across the double bond gives rise to the formation of carbocation; the methyl shift occurred which leads to stable tertiary carbocation and the nucleophilic attack of water molecule at the carbocation centre leads to the product formation followed by deprotonation. In the product, the hydrogen attached at the less substituted carbon centre and the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Acid-catalysed reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 10

The reaction of alkene with acid (as catalyst) indicates no other reagent is present. The protonation of alkene forms the secondary carbocation intermediate; the methyl shift occurred which leads to stable tertiary carbocation. The deprotonation that occur in the intermediate leads to the tetra-substituted alkene. The reaction is an alkene isomerization.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 5

Chapter 13, Problem 13.24UKC

(a)

Interpretation Introduction

Interpretation:

The IUPAC name of the given compound and the products of the given reaction to be predicted

Concept Introduction:

IUPAC naming nomenclature:

Name the parent compound: Find the longest chain containing the double bond or triple bond and add the suffix ‘-ene’ or ‘-yne’ to the end of the main chain name.

Number the carbon atoms in the main chain so that those with multiple bonds have the lowest index numbers possible:

Write the full name: List the substituents in alphabetical order. Use commas to separate the numbers and the hyphen to separate number from words. Indicate the position of double or triple bond in chain by giving the number of the first multiple-bond carbon.

Addition reaction: A general reaction type in which a substance X-Y adds to the multiple bond of an unsaturated reactant to yield a saturated product that has only single bonds.

Hydrohalogenation (Addition of hydrogen halide to alkenes): The addition of hydrogen halide to a multiple bond to give an alkyl halide product.

Hydration: The Addition of water to a multiple bond to give an alcohol product. An alkene does not react with pure water alone; it requires a small amount of acid to catalyst the reaction.

Alkene isomerization: The location of double bond is changed in the reaction process.

Markovnikov’s rule: In the addition of $HX$ to an alkene, the major product arises as the nucleophile attached to the less substituent carbon centre and hydrogen attached to the more substituent carbon centre.

(a)

Expert Solution

Answer to Problem 13.24UKC

The IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

The products obtained respectively are,

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 1

Explanation of Solution

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 2

In the given compound, the parent chain has seven carbons with the double bond between $C-2$ and C-3. The numbering done in the priority order, in which the substituents gets the lowest possible number. The parent name is 2-heptene. Include the substituents in the IUPAC name with the lowest possible number. The methyl group is located at both second and fifth carbon.

Therefore, the IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

Hydrohalogenation reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 3

In the given above reaction, the addition of $HBr$ across the double bond gives rise to the formation of carbocation, the tertiary carbocation is highly stable than the secondary carbocation and the nucleophilic attack of bromide ion at the carbocation centre leads to the product formation. In the product, the hydrogen attached at the less substituted carbon centre and thus the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Hydration reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 4

The addition of water molecule across the double bond requires small amount of acid to catalyse the reaction. In the given above reaction, the addition of acidic proton across the double bond gives rise to the formation of carbocation, the tertiary carbocation is highly stable and the nucleophilic attack of water molecule at the carbocation centre leads to the product formation followed by deprotonation. In the product, the hydrogen attached at the less substituted carbon centre and the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Acid-catalysed reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 5

The reaction of alkene with acid (as catalyst) indicates no other reagent is present. The protonation of alkene forms the tertiary carbocation intermediate. The deprotonation that occur in the intermediate leads to the di-substituted alkene. The reaction is an alkene isomerization.

(b)

Interpretation Introduction

Interpretation:

The IUPAC name of the given compound and the products of the given reaction to be predicted

Concept Introduction:

IUPAC naming nomenclature:

Name the parent compound: Find the longest chain containing the double bond or triple bond and add the suffix ‘-ene’ or ‘-yne’ to the end of the main chain name.

Number the carbon atoms in the main chain so that those with multiple bonds have the lowest index numbers possible:

Write the full name: List the substituents in alphabetical order. Use commas to separate the numbers and the hyphen to separate number from words. Indicate the position of double or triple bond in chain by giving the number of the first multiple-bond carbon.

Addition reaction: A general reaction type in which a substance X-Y adds to the multiple bond of an unsaturated reactant to yield a saturated product that has only single bonds.

Hydrohalogenation (Addition of hydrogen halide to alkenes): The addition of hydrogen halide to a multiple bond to give an alkyl halide product.

Hydration: The Addition of water to a multiple bond to give an alcohol product. An alkene does not react with pure water alone; it requires a small amount of acid to catalyst the reaction.

Alkene isomerization: The location of double bond is changed in the reaction process.

Markovnikov’s rule: In the addition of $HX$ to an alkene, the major product arises as the nucleophile attached to the less substituent carbon centre and hydrogen attached to the more substituent carbon centre.

(b)

Expert Solution

Answer to Problem 13.24UKC

The IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

The products obtained respectively are,

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 6

Explanation of Solution

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 7

In the given compound, the parent chain has five carbons with the double bond between C-1 and C-2. The numbering done in the priority order, in which the substituents gets the lowest possible number. The parent name is 1-cyclopentene. Include the substituents in the IUPAC name with the lowest possible number. Two methyl groups are located at third carbon.

Therefore, the IUPAC name of the compound is 3,3-Dimethyl-1-cyclopentene.

Hydrohalogenation reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 8

In the given above reaction, the addition of $HBr$ across the double bond gives rise to the formation of carbocation, the secondary carbocation; the methyl shift occurred which leads to stable tertiary carbocation and the nucleophilic attack of bromide ion at the carbocation centre leads to the product formation. In the product, the hydrogen attached at the less substituted carbon centre and thus the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Hydration reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 9

The addition of water molecule across the double bond requires small amount of acid to catalyse the reaction. In the given above reaction, the addition of acidic proton across the double bond gives rise to the formation of carbocation; the methyl shift occurred which leads to stable tertiary carbocation and the nucleophilic attack of water molecule at the carbocation centre leads to the product formation followed by deprotonation. In the product, the hydrogen attached at the less substituted carbon centre and the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Acid-catalysed reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 10

The reaction of alkene with acid (as catalyst) indicates no other reagent is present. The protonation of alkene forms the secondary carbocation intermediate; the methyl shift occurred which leads to stable tertiary carbocation. The deprotonation that occur in the intermediate leads to the tetra-substituted alkene. The reaction is an alkene isomerization.

Answer 6

Chapter 13, Problem 13.24UKC

(a)

Interpretation Introduction

Interpretation:

The IUPAC name of the given compound and the products of the given reaction to be predicted

Concept Introduction:

IUPAC naming nomenclature:

Name the parent compound: Find the longest chain containing the double bond or triple bond and add the suffix ‘-ene’ or ‘-yne’ to the end of the main chain name.

Number the carbon atoms in the main chain so that those with multiple bonds have the lowest index numbers possible:

Write the full name: List the substituents in alphabetical order. Use commas to separate the numbers and the hyphen to separate number from words. Indicate the position of double or triple bond in chain by giving the number of the first multiple-bond carbon.

Addition reaction: A general reaction type in which a substance X-Y adds to the multiple bond of an unsaturated reactant to yield a saturated product that has only single bonds.

Hydrohalogenation (Addition of hydrogen halide to alkenes): The addition of hydrogen halide to a multiple bond to give an alkyl halide product.

Hydration: The Addition of water to a multiple bond to give an alcohol product. An alkene does not react with pure water alone; it requires a small amount of acid to catalyst the reaction.

Alkene isomerization: The location of double bond is changed in the reaction process.

Markovnikov’s rule: In the addition of $HX$ to an alkene, the major product arises as the nucleophile attached to the less substituent carbon centre and hydrogen attached to the more substituent carbon centre.

(a)

Expert Solution

Answer to Problem 13.24UKC

The IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

The products obtained respectively are,

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 1

Explanation of Solution

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 2

In the given compound, the parent chain has seven carbons with the double bond between $C-2$ and C-3. The numbering done in the priority order, in which the substituents gets the lowest possible number. The parent name is 2-heptene. Include the substituents in the IUPAC name with the lowest possible number. The methyl group is located at both second and fifth carbon.

Therefore, the IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

Hydrohalogenation reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 3

In the given above reaction, the addition of $HBr$ across the double bond gives rise to the formation of carbocation, the tertiary carbocation is highly stable than the secondary carbocation and the nucleophilic attack of bromide ion at the carbocation centre leads to the product formation. In the product, the hydrogen attached at the less substituted carbon centre and thus the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Hydration reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 4

The addition of water molecule across the double bond requires small amount of acid to catalyse the reaction. In the given above reaction, the addition of acidic proton across the double bond gives rise to the formation of carbocation, the tertiary carbocation is highly stable and the nucleophilic attack of water molecule at the carbocation centre leads to the product formation followed by deprotonation. In the product, the hydrogen attached at the less substituted carbon centre and the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Acid-catalysed reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 5

The reaction of alkene with acid (as catalyst) indicates no other reagent is present. The protonation of alkene forms the tertiary carbocation intermediate. The deprotonation that occur in the intermediate leads to the di-substituted alkene. The reaction is an alkene isomerization.

Answer 7

Chapter 13, Problem 13.24UKC

(a)

Interpretation Introduction

Interpretation:

The IUPAC name of the given compound and the products of the given reaction to be predicted

Concept Introduction:

IUPAC naming nomenclature:

Name the parent compound: Find the longest chain containing the double bond or triple bond and add the suffix ‘-ene’ or ‘-yne’ to the end of the main chain name.

Number the carbon atoms in the main chain so that those with multiple bonds have the lowest index numbers possible:

Write the full name: List the substituents in alphabetical order. Use commas to separate the numbers and the hyphen to separate number from words. Indicate the position of double or triple bond in chain by giving the number of the first multiple-bond carbon.

Addition reaction: A general reaction type in which a substance X-Y adds to the multiple bond of an unsaturated reactant to yield a saturated product that has only single bonds.

Hydrohalogenation (Addition of hydrogen halide to alkenes): The addition of hydrogen halide to a multiple bond to give an alkyl halide product.

Hydration: The Addition of water to a multiple bond to give an alcohol product. An alkene does not react with pure water alone; it requires a small amount of acid to catalyst the reaction.

Alkene isomerization: The location of double bond is changed in the reaction process.

Markovnikov’s rule: In the addition of $HX$ to an alkene, the major product arises as the nucleophile attached to the less substituent carbon centre and hydrogen attached to the more substituent carbon centre.

Answer 8

(a)

Expert Solution

Answer to Problem 13.24UKC

The IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

The products obtained respectively are,

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 1

Answer 9

(a)

Expert Solution

Answer 10

(a)

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 2

In the given compound, the parent chain has seven carbons with the double bond between $C-2$ and C-3. The numbering done in the priority order, in which the substituents gets the lowest possible number. The parent name is 2-heptene. Include the substituents in the IUPAC name with the lowest possible number. The methyl group is located at both second and fifth carbon.

Therefore, the IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

Hydrohalogenation reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 3

In the given above reaction, the addition of $HBr$ across the double bond gives rise to the formation of carbocation, the tertiary carbocation is highly stable than the secondary carbocation and the nucleophilic attack of bromide ion at the carbocation centre leads to the product formation. In the product, the hydrogen attached at the less substituted carbon centre and thus the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Hydration reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 4

The addition of water molecule across the double bond requires small amount of acid to catalyse the reaction. In the given above reaction, the addition of acidic proton across the double bond gives rise to the formation of carbocation, the tertiary carbocation is highly stable and the nucleophilic attack of water molecule at the carbocation centre leads to the product formation followed by deprotonation. In the product, the hydrogen attached at the less substituted carbon centre and the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Acid-catalysed reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 5

The reaction of alkene with acid (as catalyst) indicates no other reagent is present. The protonation of alkene forms the tertiary carbocation intermediate. The deprotonation that occur in the intermediate leads to the di-substituted alkene. The reaction is an alkene isomerization.

Answer 13

(b)

Interpretation Introduction

Interpretation:

The IUPAC name of the given compound and the products of the given reaction to be predicted

Concept Introduction:

IUPAC naming nomenclature:

Name the parent compound: Find the longest chain containing the double bond or triple bond and add the suffix ‘-ene’ or ‘-yne’ to the end of the main chain name.

Number the carbon atoms in the main chain so that those with multiple bonds have the lowest index numbers possible:

Write the full name: List the substituents in alphabetical order. Use commas to separate the numbers and the hyphen to separate number from words. Indicate the position of double or triple bond in chain by giving the number of the first multiple-bond carbon.

Addition reaction: A general reaction type in which a substance X-Y adds to the multiple bond of an unsaturated reactant to yield a saturated product that has only single bonds.

Hydrohalogenation (Addition of hydrogen halide to alkenes): The addition of hydrogen halide to a multiple bond to give an alkyl halide product.

Hydration: The Addition of water to a multiple bond to give an alcohol product. An alkene does not react with pure water alone; it requires a small amount of acid to catalyst the reaction.

Alkene isomerization: The location of double bond is changed in the reaction process.

Markovnikov’s rule: In the addition of $HX$ to an alkene, the major product arises as the nucleophile attached to the less substituent carbon centre and hydrogen attached to the more substituent carbon centre.

(b)

Expert Solution

Answer to Problem 13.24UKC

The IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

The products obtained respectively are,

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 6

Explanation of Solution

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 7

In the given compound, the parent chain has five carbons with the double bond between C-1 and C-2. The numbering done in the priority order, in which the substituents gets the lowest possible number. The parent name is 1-cyclopentene. Include the substituents in the IUPAC name with the lowest possible number. Two methyl groups are located at third carbon.

Therefore, the IUPAC name of the compound is 3,3-Dimethyl-1-cyclopentene.

Hydrohalogenation reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 8

In the given above reaction, the addition of $HBr$ across the double bond gives rise to the formation of carbocation, the secondary carbocation; the methyl shift occurred which leads to stable tertiary carbocation and the nucleophilic attack of bromide ion at the carbocation centre leads to the product formation. In the product, the hydrogen attached at the less substituted carbon centre and thus the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Hydration reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 9

The addition of water molecule across the double bond requires small amount of acid to catalyse the reaction. In the given above reaction, the addition of acidic proton across the double bond gives rise to the formation of carbocation; the methyl shift occurred which leads to stable tertiary carbocation and the nucleophilic attack of water molecule at the carbocation centre leads to the product formation followed by deprotonation. In the product, the hydrogen attached at the less substituted carbon centre and the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Acid-catalysed reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 10

The reaction of alkene with acid (as catalyst) indicates no other reagent is present. The protonation of alkene forms the secondary carbocation intermediate; the methyl shift occurred which leads to stable tertiary carbocation. The deprotonation that occur in the intermediate leads to the tetra-substituted alkene. The reaction is an alkene isomerization.

Answer 14

(b)

Interpretation Introduction

Interpretation:

The IUPAC name of the given compound and the products of the given reaction to be predicted

Concept Introduction:

IUPAC naming nomenclature:

Name the parent compound: Find the longest chain containing the double bond or triple bond and add the suffix ‘-ene’ or ‘-yne’ to the end of the main chain name.

Number the carbon atoms in the main chain so that those with multiple bonds have the lowest index numbers possible:

Write the full name: List the substituents in alphabetical order. Use commas to separate the numbers and the hyphen to separate number from words. Indicate the position of double or triple bond in chain by giving the number of the first multiple-bond carbon.

Addition reaction: A general reaction type in which a substance X-Y adds to the multiple bond of an unsaturated reactant to yield a saturated product that has only single bonds.

Hydrohalogenation (Addition of hydrogen halide to alkenes): The addition of hydrogen halide to a multiple bond to give an alkyl halide product.

Hydration: The Addition of water to a multiple bond to give an alcohol product. An alkene does not react with pure water alone; it requires a small amount of acid to catalyst the reaction.

Alkene isomerization: The location of double bond is changed in the reaction process.

Markovnikov’s rule: In the addition of $HX$ to an alkene, the major product arises as the nucleophile attached to the less substituent carbon centre and hydrogen attached to the more substituent carbon centre.

Answer 15

(b)

Expert Solution

Answer to Problem 13.24UKC

The IUPAC name of the compound is 2,5-Dimethyl-2-heptene.

The products obtained respectively are,

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 6

Answer 16

(b)

Expert Solution

Answer 17

(b)

Expert Solution

Answer 18

Expert Solution

Answer 19

Explanation of Solution

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 7

In the given compound, the parent chain has five carbons with the double bond between C-1 and C-2. The numbering done in the priority order, in which the substituents gets the lowest possible number. The parent name is 1-cyclopentene. Include the substituents in the IUPAC name with the lowest possible number. Two methyl groups are located at third carbon.

Therefore, the IUPAC name of the compound is 3,3-Dimethyl-1-cyclopentene.

Hydrohalogenation reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 8

In the given above reaction, the addition of $HBr$ across the double bond gives rise to the formation of carbocation, the secondary carbocation; the methyl shift occurred which leads to stable tertiary carbocation and the nucleophilic attack of bromide ion at the carbocation centre leads to the product formation. In the product, the hydrogen attached at the less substituted carbon centre and thus the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Hydration reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 9

The addition of water molecule across the double bond requires small amount of acid to catalyse the reaction. In the given above reaction, the addition of acidic proton across the double bond gives rise to the formation of carbocation; the methyl shift occurred which leads to stable tertiary carbocation and the nucleophilic attack of water molecule at the carbocation centre leads to the product formation followed by deprotonation. In the product, the hydrogen attached at the less substituted carbon centre and the reaction follows Markonivok’ rule. The product obtained is MAJOR due to the high stability of carbocation formation.

Acid-catalysed reaction:

FUND.OF GEN CHEM CHAP 1-13 W/ACCESS, Chapter 13, Problem 13.24UKC , additional homework tip 10

The reaction of alkene with acid (as catalyst) indicates no other reagent is present. The protonation of alkene forms the secondary carbocation intermediate; the methyl shift occurred which leads to stable tertiary carbocation. The deprotonation that occur in the intermediate leads to the tetra-substituted alkene. The reaction is an alkene isomerization.

Answer 20

Ch. 13.2 - Prob. 13.1P Ch. 13.2 - Prob. 13.2P Ch. 13.2 - What are the IUPAC names of the two alkenes shown...Ch. 13.3 - Prob. 13.4P Ch. 13.3 - Prob. 13.5P Ch. 13.3 - Prob. 13.6KCP Ch. 13.5 - Prob. 13.7P Ch. 13.5 - Many biological transformations can be simply...Ch. 13.5 - (a) After the reaction of 11-cis-retinal with...Ch. 13.5 - Prob. 13.2CIAP

Concept explainers

Answer to Problem 13.24UKC

Explanation of Solution

Answer to Problem 13.24UKC

Explanation of Solution

Want to see more full solutions like this?

Chapter 13 Solutions