(a) Interpretation: The complete and detailed mechanism is to be drawn for the given reaction. Concept introduction: The S N 1 is an abbreviation for unimolecular nucleophilic substitution reaction. These reactions are two-step reactions. The first step is the formation of carbocation intermediate, followed by the nucleophilic attack, which is a second step. Due to the formation of a planar carbocation, the incoming nucleophile can attack the carbocation from two sides, either from the front of the plane or from the back side of the plane. This leads to give the mixture of stereoisomers. When secondary and tertiary alcohols are treated with strong concentrated acids, it follows SN1 and E1 mechanism.

Question

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Answer 1

Question

Chapter 10, Problem 10.1P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism is to be drawn for the given reaction.

Concept introduction:

The S_N1 is an abbreviation for unimolecular nucleophilic substitution reaction. These reactions are two-step reactions. The first step is the formation of carbocation intermediate, followed by the nucleophilic attack, which is a second step. Due to the formation of a planar carbocation, the incoming nucleophile can attack the carbocation from two sides, either from the front of the plane or from the back side of the plane.

This leads to give the mixture of stereoisomers. When secondary and tertiary alcohols are treated with strong concentrated acids, it follows SN1 and E1 mechanism.

Expert Solution

Answer to Problem 10.1P

The complete and detailed mechanism for given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 1

Explanation of Solution

The given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 2

The hydroxyl (-OH) group in the given substrate is a leaving group and can be protonated using concentrated strong acid, which converts it into a good leaving group.

The departure of water is a slow step that leads to formation of carbocation, and thus it is the rate-determining step. Due to the formation of planar carbocation intermediate, the incoming nucleophile can attack from either sides, either the top (from above the plane) or bottom (from below of plane). The bromide ion formed in the proton transfer step is the attacking species in the second step of the mechanism. In the second step, the bromide ion (Br- ) attacks the planar carbocation to form a mixture of stereoisomers.

Both top and bottom attack of nucleophile are possible leads to formation of the mixture of isomers, as shown below:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 3

Conclusion

Due to the formation of carbocation intermediate in S_N1 reaction, a mixture of stereoisomer is produced.

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism is to be drawn for the given reaction.

Concept introduction:

The S_N1 is an abbreviation for unimolecular nucleophilic substitution reaction. These reactions are two-step reactions. The first step is the formation of carbocation intermediate, followed by the nucleophilic attack of attacking species, which is a second step. Due to the formation of a planar carbocation, the incoming nucleophile can attack the carbocation from two sides, either from the front of the plane or from the back side of the plane.

This leads to give the mixture of stereoisomers. When secondary and tertiary alcohols are treated with strong concentrated acids, it follows SN1 and E1 mechanism.

Expert Solution

Answer to Problem 10.1P

The complete and detailed mechanism for given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 4

Explanation of Solution

The given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 5

The hydroxyl (-OH) group in the given substrate is not a good leaving group. But it can be converted into a good leaving group by treating it with a concentrated strong acid. Thus, the first step of the mechanism should be a proton transfer reaction which protonates the -OH group and converts it into H2O+ (water molecule), which is an excellent leaving group. The departure of water is a slow step, which leads to the formation of carbocation intermediate. The carbocation intermediate is sp2 hybridized and has a planar geometry. The planar geometry of the resulting carbocation intermediate enables the attack of the nucleophile from either sides of the plane. The incoming nucleophile can attack either from the top (from above the plane) or bottom (from below of plane) of the plane. The bromide ion formed in the proton transfer step is the attacking species in the second step of the mechanism. In the second step, bromide ion (Br- ) attacks the planar carbocation to form a mixture of stereoisomers.

Both top and bottom attack of nucleophile are possible leads to formation of the mixture of isomers, as shown below:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 6

Conclusion

Due to the formation of carbocation intermediate in S_N1 reaction, a mixture of stereoisomer is produced.

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For each scenario below, select the color of the solution using the indicator thymol blue during the titration. When you first add indicator to your Na2CO3solution, the solution is basic (pH ~10), and the color is ["", "", "", "", ""] . At the equivalence point for the titration, the moles of added HCl are equal to the moles of Na2CO3. One drop (or less!) past this is called the endpoint. The added HCl begins to titrate the thymol blue indicator itself. At the endpoint, the indicator color is ["", "", "", "", ""] . When you weren't paying attention and added too much HCl (~12 mL extra), the color is ["", "", "", "", ""] . When you really weren't paying attention and reached the second equivalence point of Na2CO3, the color is

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Answer 2

Question

Chapter 10, Problem 10.1P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism is to be drawn for the given reaction.

Concept introduction:

The S_N1 is an abbreviation for unimolecular nucleophilic substitution reaction. These reactions are two-step reactions. The first step is the formation of carbocation intermediate, followed by the nucleophilic attack, which is a second step. Due to the formation of a planar carbocation, the incoming nucleophile can attack the carbocation from two sides, either from the front of the plane or from the back side of the plane.

This leads to give the mixture of stereoisomers. When secondary and tertiary alcohols are treated with strong concentrated acids, it follows SN1 and E1 mechanism.

Expert Solution

Answer to Problem 10.1P

The complete and detailed mechanism for given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 1

Explanation of Solution

The given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 2

The hydroxyl (-OH) group in the given substrate is a leaving group and can be protonated using concentrated strong acid, which converts it into a good leaving group.

The departure of water is a slow step that leads to formation of carbocation, and thus it is the rate-determining step. Due to the formation of planar carbocation intermediate, the incoming nucleophile can attack from either sides, either the top (from above the plane) or bottom (from below of plane). The bromide ion formed in the proton transfer step is the attacking species in the second step of the mechanism. In the second step, the bromide ion (Br- ) attacks the planar carbocation to form a mixture of stereoisomers.

Both top and bottom attack of nucleophile are possible leads to formation of the mixture of isomers, as shown below:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 3

Conclusion

Due to the formation of carbocation intermediate in S_N1 reaction, a mixture of stereoisomer is produced.

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism is to be drawn for the given reaction.

Concept introduction:

The S_N1 is an abbreviation for unimolecular nucleophilic substitution reaction. These reactions are two-step reactions. The first step is the formation of carbocation intermediate, followed by the nucleophilic attack of attacking species, which is a second step. Due to the formation of a planar carbocation, the incoming nucleophile can attack the carbocation from two sides, either from the front of the plane or from the back side of the plane.

This leads to give the mixture of stereoisomers. When secondary and tertiary alcohols are treated with strong concentrated acids, it follows SN1 and E1 mechanism.

Expert Solution

Answer to Problem 10.1P

The complete and detailed mechanism for given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 4

Explanation of Solution

The given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 5

The hydroxyl (-OH) group in the given substrate is not a good leaving group. But it can be converted into a good leaving group by treating it with a concentrated strong acid. Thus, the first step of the mechanism should be a proton transfer reaction which protonates the -OH group and converts it into H2O+ (water molecule), which is an excellent leaving group. The departure of water is a slow step, which leads to the formation of carbocation intermediate. The carbocation intermediate is sp2 hybridized and has a planar geometry. The planar geometry of the resulting carbocation intermediate enables the attack of the nucleophile from either sides of the plane. The incoming nucleophile can attack either from the top (from above the plane) or bottom (from below of plane) of the plane. The bromide ion formed in the proton transfer step is the attacking species in the second step of the mechanism. In the second step, bromide ion (Br- ) attacks the planar carbocation to form a mixture of stereoisomers.

Both top and bottom attack of nucleophile are possible leads to formation of the mixture of isomers, as shown below:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 6

Conclusion

Due to the formation of carbocation intermediate in S_N1 reaction, a mixture of stereoisomer is produced.

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Answer 3

Question

Chapter 10, Problem 10.1P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism is to be drawn for the given reaction.

Concept introduction:

The S_N1 is an abbreviation for unimolecular nucleophilic substitution reaction. These reactions are two-step reactions. The first step is the formation of carbocation intermediate, followed by the nucleophilic attack, which is a second step. Due to the formation of a planar carbocation, the incoming nucleophile can attack the carbocation from two sides, either from the front of the plane or from the back side of the plane.

This leads to give the mixture of stereoisomers. When secondary and tertiary alcohols are treated with strong concentrated acids, it follows SN1 and E1 mechanism.

Expert Solution

Answer to Problem 10.1P

The complete and detailed mechanism for given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 1

Explanation of Solution

The given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 2

The hydroxyl (-OH) group in the given substrate is a leaving group and can be protonated using concentrated strong acid, which converts it into a good leaving group.

The departure of water is a slow step that leads to formation of carbocation, and thus it is the rate-determining step. Due to the formation of planar carbocation intermediate, the incoming nucleophile can attack from either sides, either the top (from above the plane) or bottom (from below of plane). The bromide ion formed in the proton transfer step is the attacking species in the second step of the mechanism. In the second step, the bromide ion (Br- ) attacks the planar carbocation to form a mixture of stereoisomers.

Both top and bottom attack of nucleophile are possible leads to formation of the mixture of isomers, as shown below:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 3

Conclusion

Due to the formation of carbocation intermediate in S_N1 reaction, a mixture of stereoisomer is produced.

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism is to be drawn for the given reaction.

Concept introduction:

The S_N1 is an abbreviation for unimolecular nucleophilic substitution reaction. These reactions are two-step reactions. The first step is the formation of carbocation intermediate, followed by the nucleophilic attack of attacking species, which is a second step. Due to the formation of a planar carbocation, the incoming nucleophile can attack the carbocation from two sides, either from the front of the plane or from the back side of the plane.

This leads to give the mixture of stereoisomers. When secondary and tertiary alcohols are treated with strong concentrated acids, it follows SN1 and E1 mechanism.

Expert Solution

Answer to Problem 10.1P

The complete and detailed mechanism for given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 4

Explanation of Solution

The given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 5

The hydroxyl (-OH) group in the given substrate is not a good leaving group. But it can be converted into a good leaving group by treating it with a concentrated strong acid. Thus, the first step of the mechanism should be a proton transfer reaction which protonates the -OH group and converts it into H2O+ (water molecule), which is an excellent leaving group. The departure of water is a slow step, which leads to the formation of carbocation intermediate. The carbocation intermediate is sp2 hybridized and has a planar geometry. The planar geometry of the resulting carbocation intermediate enables the attack of the nucleophile from either sides of the plane. The incoming nucleophile can attack either from the top (from above the plane) or bottom (from below of plane) of the plane. The bromide ion formed in the proton transfer step is the attacking species in the second step of the mechanism. In the second step, bromide ion (Br- ) attacks the planar carbocation to form a mixture of stereoisomers.

Both top and bottom attack of nucleophile are possible leads to formation of the mixture of isomers, as shown below:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 6

Conclusion

Due to the formation of carbocation intermediate in S_N1 reaction, a mixture of stereoisomer is produced.

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 10, Problem 10.1P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism is to be drawn for the given reaction.

Concept introduction:

The S_N1 is an abbreviation for unimolecular nucleophilic substitution reaction. These reactions are two-step reactions. The first step is the formation of carbocation intermediate, followed by the nucleophilic attack, which is a second step. Due to the formation of a planar carbocation, the incoming nucleophile can attack the carbocation from two sides, either from the front of the plane or from the back side of the plane.

This leads to give the mixture of stereoisomers. When secondary and tertiary alcohols are treated with strong concentrated acids, it follows SN1 and E1 mechanism.

Expert Solution

Answer to Problem 10.1P

The complete and detailed mechanism for given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 1

Explanation of Solution

The given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 2

The hydroxyl (-OH) group in the given substrate is a leaving group and can be protonated using concentrated strong acid, which converts it into a good leaving group.

The departure of water is a slow step that leads to formation of carbocation, and thus it is the rate-determining step. Due to the formation of planar carbocation intermediate, the incoming nucleophile can attack from either sides, either the top (from above the plane) or bottom (from below of plane). The bromide ion formed in the proton transfer step is the attacking species in the second step of the mechanism. In the second step, the bromide ion (Br- ) attacks the planar carbocation to form a mixture of stereoisomers.

Both top and bottom attack of nucleophile are possible leads to formation of the mixture of isomers, as shown below:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 3

Conclusion

Due to the formation of carbocation intermediate in S_N1 reaction, a mixture of stereoisomer is produced.

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism is to be drawn for the given reaction.

Concept introduction:

The S_N1 is an abbreviation for unimolecular nucleophilic substitution reaction. These reactions are two-step reactions. The first step is the formation of carbocation intermediate, followed by the nucleophilic attack of attacking species, which is a second step. Due to the formation of a planar carbocation, the incoming nucleophile can attack the carbocation from two sides, either from the front of the plane or from the back side of the plane.

This leads to give the mixture of stereoisomers. When secondary and tertiary alcohols are treated with strong concentrated acids, it follows SN1 and E1 mechanism.

Expert Solution

Answer to Problem 10.1P

The complete and detailed mechanism for given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 4

Explanation of Solution

The given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 5

The hydroxyl (-OH) group in the given substrate is not a good leaving group. But it can be converted into a good leaving group by treating it with a concentrated strong acid. Thus, the first step of the mechanism should be a proton transfer reaction which protonates the -OH group and converts it into H2O+ (water molecule), which is an excellent leaving group. The departure of water is a slow step, which leads to the formation of carbocation intermediate. The carbocation intermediate is sp2 hybridized and has a planar geometry. The planar geometry of the resulting carbocation intermediate enables the attack of the nucleophile from either sides of the plane. The incoming nucleophile can attack either from the top (from above the plane) or bottom (from below of plane) of the plane. The bromide ion formed in the proton transfer step is the attacking species in the second step of the mechanism. In the second step, bromide ion (Br- ) attacks the planar carbocation to form a mixture of stereoisomers.

Both top and bottom attack of nucleophile are possible leads to formation of the mixture of isomers, as shown below:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 6

Conclusion

Due to the formation of carbocation intermediate in S_N1 reaction, a mixture of stereoisomer is produced.

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

Answer 5

Chapter 10, Problem 10.1P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism is to be drawn for the given reaction.

Concept introduction:

The S_N1 is an abbreviation for unimolecular nucleophilic substitution reaction. These reactions are two-step reactions. The first step is the formation of carbocation intermediate, followed by the nucleophilic attack, which is a second step. Due to the formation of a planar carbocation, the incoming nucleophile can attack the carbocation from two sides, either from the front of the plane or from the back side of the plane.

This leads to give the mixture of stereoisomers. When secondary and tertiary alcohols are treated with strong concentrated acids, it follows SN1 and E1 mechanism.

Expert Solution

Answer to Problem 10.1P

The complete and detailed mechanism for given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 1

Explanation of Solution

The given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 2

The hydroxyl (-OH) group in the given substrate is a leaving group and can be protonated using concentrated strong acid, which converts it into a good leaving group.

The departure of water is a slow step that leads to formation of carbocation, and thus it is the rate-determining step. Due to the formation of planar carbocation intermediate, the incoming nucleophile can attack from either sides, either the top (from above the plane) or bottom (from below of plane). The bromide ion formed in the proton transfer step is the attacking species in the second step of the mechanism. In the second step, the bromide ion (Br- ) attacks the planar carbocation to form a mixture of stereoisomers.

Both top and bottom attack of nucleophile are possible leads to formation of the mixture of isomers, as shown below:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 3

Conclusion

Due to the formation of carbocation intermediate in S_N1 reaction, a mixture of stereoisomer is produced.

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism is to be drawn for the given reaction.

Concept introduction:

The S_N1 is an abbreviation for unimolecular nucleophilic substitution reaction. These reactions are two-step reactions. The first step is the formation of carbocation intermediate, followed by the nucleophilic attack of attacking species, which is a second step. Due to the formation of a planar carbocation, the incoming nucleophile can attack the carbocation from two sides, either from the front of the plane or from the back side of the plane.

This leads to give the mixture of stereoisomers. When secondary and tertiary alcohols are treated with strong concentrated acids, it follows SN1 and E1 mechanism.

Expert Solution

Answer to Problem 10.1P

The complete and detailed mechanism for given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 4

Explanation of Solution

The given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 5

The hydroxyl (-OH) group in the given substrate is not a good leaving group. But it can be converted into a good leaving group by treating it with a concentrated strong acid. Thus, the first step of the mechanism should be a proton transfer reaction which protonates the -OH group and converts it into H2O+ (water molecule), which is an excellent leaving group. The departure of water is a slow step, which leads to the formation of carbocation intermediate. The carbocation intermediate is sp2 hybridized and has a planar geometry. The planar geometry of the resulting carbocation intermediate enables the attack of the nucleophile from either sides of the plane. The incoming nucleophile can attack either from the top (from above the plane) or bottom (from below of plane) of the plane. The bromide ion formed in the proton transfer step is the attacking species in the second step of the mechanism. In the second step, bromide ion (Br- ) attacks the planar carbocation to form a mixture of stereoisomers.

Both top and bottom attack of nucleophile are possible leads to formation of the mixture of isomers, as shown below:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 6

Conclusion

Due to the formation of carbocation intermediate in S_N1 reaction, a mixture of stereoisomer is produced.

Answer 6

Chapter 10, Problem 10.1P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism is to be drawn for the given reaction.

Concept introduction:

The S_N1 is an abbreviation for unimolecular nucleophilic substitution reaction. These reactions are two-step reactions. The first step is the formation of carbocation intermediate, followed by the nucleophilic attack, which is a second step. Due to the formation of a planar carbocation, the incoming nucleophile can attack the carbocation from two sides, either from the front of the plane or from the back side of the plane.

This leads to give the mixture of stereoisomers. When secondary and tertiary alcohols are treated with strong concentrated acids, it follows SN1 and E1 mechanism.

Expert Solution

Answer to Problem 10.1P

The complete and detailed mechanism for given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 1

Explanation of Solution

The given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 2

The hydroxyl (-OH) group in the given substrate is a leaving group and can be protonated using concentrated strong acid, which converts it into a good leaving group.

The departure of water is a slow step that leads to formation of carbocation, and thus it is the rate-determining step. Due to the formation of planar carbocation intermediate, the incoming nucleophile can attack from either sides, either the top (from above the plane) or bottom (from below of plane). The bromide ion formed in the proton transfer step is the attacking species in the second step of the mechanism. In the second step, the bromide ion (Br- ) attacks the planar carbocation to form a mixture of stereoisomers.

Both top and bottom attack of nucleophile are possible leads to formation of the mixture of isomers, as shown below:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 3

Conclusion

Due to the formation of carbocation intermediate in S_N1 reaction, a mixture of stereoisomer is produced.

Answer 7

Chapter 10, Problem 10.1P

Interpretation Introduction

(a)

Interpretation:

The complete and detailed mechanism is to be drawn for the given reaction.

Concept introduction:

The S_N1 is an abbreviation for unimolecular nucleophilic substitution reaction. These reactions are two-step reactions. The first step is the formation of carbocation intermediate, followed by the nucleophilic attack, which is a second step. Due to the formation of a planar carbocation, the incoming nucleophile can attack the carbocation from two sides, either from the front of the plane or from the back side of the plane.

This leads to give the mixture of stereoisomers. When secondary and tertiary alcohols are treated with strong concentrated acids, it follows SN1 and E1 mechanism.

Answer 8

Expert Solution

Answer to Problem 10.1P

The complete and detailed mechanism for given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 1

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

The given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 2

The hydroxyl (-OH) group in the given substrate is a leaving group and can be protonated using concentrated strong acid, which converts it into a good leaving group.

The departure of water is a slow step that leads to formation of carbocation, and thus it is the rate-determining step. Due to the formation of planar carbocation intermediate, the incoming nucleophile can attack from either sides, either the top (from above the plane) or bottom (from below of plane). The bromide ion formed in the proton transfer step is the attacking species in the second step of the mechanism. In the second step, the bromide ion (Br- ) attacks the planar carbocation to form a mixture of stereoisomers.

Both top and bottom attack of nucleophile are possible leads to formation of the mixture of isomers, as shown below:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 3

Answer 13

Conclusion

Due to the formation of carbocation intermediate in S_N1 reaction, a mixture of stereoisomer is produced.

Answer 14

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism is to be drawn for the given reaction.

Concept introduction:

The S_N1 is an abbreviation for unimolecular nucleophilic substitution reaction. These reactions are two-step reactions. The first step is the formation of carbocation intermediate, followed by the nucleophilic attack of attacking species, which is a second step. Due to the formation of a planar carbocation, the incoming nucleophile can attack the carbocation from two sides, either from the front of the plane or from the back side of the plane.

This leads to give the mixture of stereoisomers. When secondary and tertiary alcohols are treated with strong concentrated acids, it follows SN1 and E1 mechanism.

Expert Solution

Answer to Problem 10.1P

The complete and detailed mechanism for given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 4

Explanation of Solution

The given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 5

The hydroxyl (-OH) group in the given substrate is not a good leaving group. But it can be converted into a good leaving group by treating it with a concentrated strong acid. Thus, the first step of the mechanism should be a proton transfer reaction which protonates the -OH group and converts it into H2O+ (water molecule), which is an excellent leaving group. The departure of water is a slow step, which leads to the formation of carbocation intermediate. The carbocation intermediate is sp2 hybridized and has a planar geometry. The planar geometry of the resulting carbocation intermediate enables the attack of the nucleophile from either sides of the plane. The incoming nucleophile can attack either from the top (from above the plane) or bottom (from below of plane) of the plane. The bromide ion formed in the proton transfer step is the attacking species in the second step of the mechanism. In the second step, bromide ion (Br- ) attacks the planar carbocation to form a mixture of stereoisomers.

Both top and bottom attack of nucleophile are possible leads to formation of the mixture of isomers, as shown below:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 6

Conclusion

Due to the formation of carbocation intermediate in S_N1 reaction, a mixture of stereoisomer is produced.

Answer 15

Interpretation Introduction

(b)

Interpretation:

The complete and detailed mechanism is to be drawn for the given reaction.

Concept introduction:

The S_N1 is an abbreviation for unimolecular nucleophilic substitution reaction. These reactions are two-step reactions. The first step is the formation of carbocation intermediate, followed by the nucleophilic attack of attacking species, which is a second step. Due to the formation of a planar carbocation, the incoming nucleophile can attack the carbocation from two sides, either from the front of the plane or from the back side of the plane.

This leads to give the mixture of stereoisomers. When secondary and tertiary alcohols are treated with strong concentrated acids, it follows SN1 and E1 mechanism.

Answer 16

Expert Solution

Answer to Problem 10.1P

The complete and detailed mechanism for given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 4

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

The given reaction is as follows:

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M, Chapter 10, Problem 10.1P , additional homework tip 5

The hydroxyl (-OH) group in the given substrate is not a good leaving group. But it can be converted into a good leaving group by treating it with a concentrated strong acid. Thus, the first step of the mechanism should be a proton transfer reaction which protonates the -OH group and converts it into H2O+ (water molecule), which is an excellent leaving group. The departure of water is a slow step, which leads to the formation of carbocation intermediate. The carbocation intermediate is sp2 hybridized and has a planar geometry. The planar geometry of the resulting carbocation intermediate enables the attack of the nucleophile from either sides of the plane. The incoming nucleophile can attack either from the top (from above the plane) or bottom (from below of plane) of the plane. The bromide ion formed in the proton transfer step is the attacking species in the second step of the mechanism. In the second step, bromide ion (Br- ) attacks the planar carbocation to form a mixture of stereoisomers.