Chapter 10, Problem 10.57P

Interpretation Introduction

(a)

Interpretation: The products for the given reaction including stereoisomers are to be drawn.

Concept introduction: Hydration of alkenes is one of the methods used for the formation of alcohol.

The general steps involved in the hydration reaction are stated below:

• First, protonation of the alkene takes place to generate the carbocation.

• Formation of protonated alcohol.

• Deprotonation.

In this type of reaction, hydroxyl group attacks on the more substituted carbon.

Stereochemistry is defined as the arrangement of molecules in three dimensional space and its impact on chemical reactions. Stereochemistry for the products is shown by the dashed and wedge lines. Dashed lines represent that the bond is far away from the plane, whereas wedge line represents the bond out of the plane and towards the observer. These lines are used to represent the stereochemistry of the compound.

Answer to Problem 10.57P

The products for the given reaction including stereoisomers are shown below.

Explanation of Solution

Hydration of alkenes is one of the methods used for the formation of alcohol.

The general steps involved in the hydration reaction are stated below:

• First, protonation of the alkene takes place to generate the carbocation.

• Formation of protonated alcohol.

• Deprotonation.

In this type of reaction, hydroxyl group attacks on the more substituted carbon.

The given reaction is,

Figure 1

The products for the given reaction including stereoisomers are shown below.

Figure 2

Conclusion

The products for the given reaction including stereoisomers are shown in Figure 2.

Interpretation Introduction

(b)

Interpretation: The products for the given reaction including stereoisomers are to be drawn.

Concept introduction: The reaction of hydrogen halide with alkene results in the formation of alkyl halide. This type of reaction is an electrophilic addition of hydrogen halide.

Electrophilic addition reactions are those in which breaking of pi bond takes place to form new sigma bond. In this type of reaction, carbocation is formed during the formation of new bond.

Answer to Problem 10.57P

The products for the given reaction including stereoisomers are shown below.

Explanation of Solution

Electrophilic addition reaction follows Markovnikov’s rule. According to Markovnikov’s rule, the positive part of halogen acid attached to that carbon atom in $\text{C}=\text{C}$ bond which carries maximum number of hydrogen atoms and the negative part of halogen acid will attach to that carbon atom in $\text{C}=\text{C}$ bond which has minimum number of hydrogen atoms.

The steps involved in the electrophilic addition reaction are stated below:

• First, protonation of the alkene takes place to generate the carbocation.

• The halide ion will attack on the carbocation to give the final product.

The given reaction is,

Figure 3

The products for the given reaction including stereoisomers are shown below.

Figure 4

Conclusion

The products for the given reaction including stereoisomers are shown in Figure 4.

Interpretation Introduction

(c)

Interpretation: The products for the given reaction including stereoisomers are to be drawn.

Concept introduction: The addition of Halogens to alkenes is a stereospecific reaction. The resultant product is meso compound, if alkene is cis and addition of halogen is syn addition. If addition of halogen is anti, then the resultant products are racemic mixture. In case of trans alkene, the resultant product is meso, if addition of halogen is anti. The resultant products are racemic mixture, if the addition of halogen is syn.

Answer to Problem 10.57P

The products for the given reaction including stereoisomers are shown below.

Explanation of Solution

The general steps involved in the addition of Halogens to alkenes are stated below:

• The first step is the electrophilic attack of halide ion to form a halonium ion.

• The second step is the attack of halide ion from back side to open the halonium ion.

The given reaction is,

Figure 5

The products for the given reaction including stereoisomers are shown below.

Figure 6

Conclusion

The products for the given reaction including stereoisomers are shown in Figure 6.

Interpretation Introduction

(d)

Interpretation: The products for the given reaction including stereoisomers are to be drawn.

Concept introduction: Hydroboration reaction is a two step reaction, which involves conversion of alkene into alcohol. This type of reaction follows anti-Markovnikov’s rule.

Anti markovnikov rule states that the positive part of acid gets attached to that carbon atom in $\text{C}=\text{C}$ bond which carries lesser number of hydrogen atoms and the negative part of acid will attach to that carbon atom in $\text{C}=\text{C}$ bond which has more number of hydrogen atoms.

Anti addition is the addition of any atom from the opposite faces of the double bond of alkene, whereas syn addition is the addition of atom from the same side.

Answer to Problem 10.57P

The products for the given reaction including stereoisomers are given below.

Explanation of Solution

During hydroboration reaction, if boron and hydrogen adds to the double bond of alkene from the same side then it leads to formation of syn addition, whereas if they add from the opposite side then it leads to anti-addition.

The given reaction is,

Figure 7

The products for the given reaction including stereoisomers are shown below.

Figure 8

Conclusion

The products for the given reaction including stereoisomers are shown in Figure 8.

Interpretation Introduction

(e)

Interpretation: The products for the given reaction including stereoisomers are to be drawn.

Concept introduction: The reaction of alkene with halogen and water results in the formation of halohydrin product.

Stereochemistry is defined as the arrangement of molecules in three dimensional space and its impact on chemical reactions. Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene, whereas syn addition is the addition of atom from the same side.

The general steps for the formation of halohydrin are stated below:

• The first step is the attack of halide ion to form a halonium ion.

• The second step is the attack of water from back side to open the halonium ion.

• The last step is deprotonation to give the halohydrin product.

Answer to Problem 10.57P

The product for the given reaction including stereoisomers is given below.

Explanation of Solution

The addition of halogens to alkenes is a stereospecific reaction. The resultant product is meso compound, if alkene is cis and addition of halogen is syn addition. If addition of halogen is anti, then the resultant products are racemic mixture. In case of trans alkene, the resultant product is meso, if addition of halogen is anti. The resultant products are racemic mixture, if the addition of halogen is syn addition.

The given reaction is,

Figure 9

The general steps for the formation of halohydrin are stated below:

• The first step is the attack of halide ion to form a halonium ion.

• The second step is the attack of water from back side to open the halonium ion.

• The last step is deprotonation to give the halohydrin product.

The products for the given reaction including stereoisomers are shown below.

Figure 10

Conclusion

The products for the given reaction including stereoisomers are shown in Figure 10.

Interpretation Introduction

(f)

Interpretation: The products for the given reaction including stereoisomers are to be drawn.

Concept introduction: The reaction of alkene with halogen and water results in the formation of halohydrin product.

Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions. Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene, whereas syn addition is the addition of atom from the same side.

The general steps for the formation of halohydrin are stated below:

• The first step is the attack of halide ion to form a halonium ion.

• The second step is the attack of water from back side to open the halonium ion.

• The last step is deprotonation to give the halohydrin product.

Answer to Problem 10.57P

The product for the given reaction including stereoisomers is given below.

Explanation of Solution

The addition of halogens to alkenes is a stereospecific reaction. The resultant product is meso compound, if alkene is cis and addition of halogen is syn addition. If addition of halogen is anti, then the resultant products are racemic mixture. In case of trans alkene, the resultant product is meso, if addition of halogen is anti. The resultant products are racemic mixture, if the addition of halogen is syn addition.

The given reaction is,

Figure 11

The general steps for the formation of halohydrin are stated below:

• The first step is the attack of halide ion to form a halonium ion.

• The second step is the attack of water from back side to open the halonium ion.

• The last step is deprotonation to give the halohydrin product.

The products for the given reaction including stereoisomers are shown below.

Figure 12

Conclusion

The products for the given reaction including stereoisomers are shown in figure 12.

Interpretation Introduction

(g)

Interpretation: The products for the given reaction including stereoisomers are to be drawn.

Concept introduction: Hydration of alkenes is one of the methods used for the formation of alcohol.

The general steps followed by hydration reaction are stated below:

• First, protonation of the alkene takes place to generate the carbocation.

• Formation of protonated alcohol.

• Deprotonation.

In this type of reaction, hydroxyl group attacks on the more substituted carbon.

Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions. Stereochemistry for the products is shown by the dashed and wedge lines. Dashed lines represent that the bond is far away from the plane, whereas wedge line represents the bond out of the plane and towards the observer. These lines are used to represent the stereochemistry of the compound.

Answer to Problem 10.57P

The products for the given reaction including stereoisomers are shown below.

Explanation of Solution

The addition of Halogens to alkenes is a stereospecific reaction. The resultant product is meso compound, if alkene is cis and addition of halogen is syn addition. If addition of halogen is anti, then the resultant products are racemic mixture. In case of trans alkene, the resultant product is meso, if addition of halogen is anti. The resultant products are racemic mixture, if the addition of halogen is syn addition.

The given reaction is,

Figure 13

The reaction of $N-\text{bromosuccinimide}$ in aqueous DMSO results in the formation of bromohydrins. $\text{NBS}$ is the source of ${\text{Br}}_{\text{2}}$ as shown below.

Figure 14

The general steps for the formation of halohydrin are stated below:

• The first step is the attack of halide ion to form a halonium ion.

• The second step is the attack of water from back side to open the halonium ion.

• The last step is deprotonation to give the halohydrin product.

The products for the given reaction including stereoisomers are shown below.

Figure 15

The attack of water on halonium ion is from back side that opens the bromonium ion to form mixture of enantiomers. This shows that the mode of addition in this reaction is anti which gives trans enantiomers.

Conclusion

The products for the given reaction including stereoisomers are shown in figure 15.

Interpretation Introduction

(h)

Interpretation: The products for the given reaction including stereoisomers are to be drawn.

Concept introduction: Hydration of alkenes is one of the methods used for the formation of alcohol.

The general steps followed by hydration reaction are stated below:

• First, protonation of the alkene takes place to generate the carbocation.

• Formation of protonated alcohol.

• Deprotonation.

In this type of reaction, hydroxyl group attacks on the more substituted carbon.

Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions. Stereochemistry for the products is shown by the dashed and wedge lines. Dashed lines represent that the bond is far away from the plane, whereas wedge line represents the bond out of the plane and towards the observer. These lines are used to represent the stereochemistry of the compound.

Answer to Problem 10.57P

The products for the given reaction including stereoisomers are shown below.

Explanation of Solution

Hydration of alkenes is one of the methods used for the formation of alcohol.

The general steps followed by hydration reaction are stated below:

• First, protonation of the alkene takes place to generate the carbocation.

• Formation of protonated alcohol.

• Deprotonation.

In this type of reaction, hydroxyl group attacks on the more substituted carbon.

The given reaction is,

Figure 16

The products for the given reaction including stereoisomers are shown below.

Figure 17

Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions. Stereochemistry for the products is shown by the dashed and wedge lines. Dashed lines represent that the bond is far away from the plane, whereas wedge line represents the bond out of the plane and towards the observer. These lines are used to represent the stereochemistry of the compound.

Conclusion

The products for the given reaction including stereoisomers are shown in figure 17.