Structures of the principle organic products in each of the given reactions is to be determined. Concept introduction: Since alkenes have the capacity to react with substances that add to them, they are unsaturated hydrocarbons. Therefore, alkenes show addition reactions. According to Markovnikov’s rule. when an unsymmetrically substituted alkene reacts with a hydrogen halide, hydrogen adds to the carbon that has the greater number of hydrogens and halogen adds to the carbon that has fewer hydrogens. In hydroboration-oxidation reaction, hydrogen atom gets bonded to the carbon that has fewer hydrogens and the hydroxyl to the carbon that has a greater number of hydrogens. This is a rule opposite of Markovnikov’s addition.

Question

Consider the compound C5H9Br (Compound X). It reacts with potassium tert-butoxide to give Compound Y, C5H8. Compound Y upon reaction with hydrogen produced methylcyclobutane. Compound Y upon reaction with ozone produces one compound with two aldehyde functional groups. Provide the structures of Compound X and Y.

Answer 1

Question

Definition Definition Molecules that have multiple bonds between their carbon atoms. Alkenes are hydrocarbons with a double bond between two adjacent carbon atoms (R 2 C=CR 2 ), whereas alkynes are hydrocarbons with a triple bond between two adjacent carbon atoms R-C=C-R . These two groups are known as unsaturated hydrocarbons. They have fewer hydrogen atoms when compared with alkanes with same number of carbon atoms. The general molecular formula for an unsaturated hydrocarbon can be represented as C n H 2n +2 .

Chapter 8, Problem 31P

Interpretation Introduction

Interpretation:

Structures of the principle organic products in each of the given reactions is to be determined.

Concept introduction:

Since alkenes have the capacity to react with substances that add to them, they are unsaturated hydrocarbons. Therefore, alkenes show addition reactions.

According to Markovnikov’s rule. when an unsymmetrically substituted alkene reacts with a hydrogen halide, hydrogen adds to the carbon that has the greater number of hydrogens and halogen adds to the carbon that has fewer hydrogens.

In hydroboration-oxidation reaction, hydrogen atom gets bonded to the carbon that has fewer hydrogens and the hydroxyl to the carbon that has a greater number of hydrogens. This is a rule opposite of Markovnikov’s addition.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Consider the compound C5H9Br (Compound X). It reacts with potassium tert-butoxide to give Compound Y, C5H8. Compound Y upon reaction with hydrogen produced methylcyclobutane. Compound Y upon reaction with ozone produces one compound with two aldehyde functional groups. Provide the structures of Compound X and Y.

The following reaction has been reported in the chemical literature and gives a single organic product in high yield. Write the structure of the product for the reaction of 2−phenylpropene treated with diborane in tetrahydrofuran followed by oxidation with basic hydrogen peroxide.

An unknown hydrocarbon Q has a formula C6H12. Q reacts with osmium tetroxide to give a diol R when oxidized with KMnQ4 in an acidic medium Q gives two products. One product is propanoic acid and the other is ketone S. Provide reaction equations to identify the possible structures of Q, R and S.

Answer 2

Question

Definition Definition Molecules that have multiple bonds between their carbon atoms. Alkenes are hydrocarbons with a double bond between two adjacent carbon atoms (R 2 C=CR 2 ), whereas alkynes are hydrocarbons with a triple bond between two adjacent carbon atoms R-C=C-R . These two groups are known as unsaturated hydrocarbons. They have fewer hydrogen atoms when compared with alkanes with same number of carbon atoms. The general molecular formula for an unsaturated hydrocarbon can be represented as C n H 2n +2 .

Chapter 8, Problem 31P

Interpretation Introduction

Interpretation:

Structures of the principle organic products in each of the given reactions is to be determined.

Concept introduction:

Since alkenes have the capacity to react with substances that add to them, they are unsaturated hydrocarbons. Therefore, alkenes show addition reactions.

According to Markovnikov’s rule. when an unsymmetrically substituted alkene reacts with a hydrogen halide, hydrogen adds to the carbon that has the greater number of hydrogens and halogen adds to the carbon that has fewer hydrogens.

In hydroboration-oxidation reaction, hydrogen atom gets bonded to the carbon that has fewer hydrogens and the hydroxyl to the carbon that has a greater number of hydrogens. This is a rule opposite of Markovnikov’s addition.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 3

Question

Definition Definition Molecules that have multiple bonds between their carbon atoms. Alkenes are hydrocarbons with a double bond between two adjacent carbon atoms (R 2 C=CR 2 ), whereas alkynes are hydrocarbons with a triple bond between two adjacent carbon atoms R-C=C-R . These two groups are known as unsaturated hydrocarbons. They have fewer hydrogen atoms when compared with alkanes with same number of carbon atoms. The general molecular formula for an unsaturated hydrocarbon can be represented as C n H 2n +2 .

Chapter 8, Problem 31P

Interpretation Introduction

Interpretation:

Structures of the principle organic products in each of the given reactions is to be determined.

Concept introduction:

Since alkenes have the capacity to react with substances that add to them, they are unsaturated hydrocarbons. Therefore, alkenes show addition reactions.

According to Markovnikov’s rule. when an unsymmetrically substituted alkene reacts with a hydrogen halide, hydrogen adds to the carbon that has the greater number of hydrogens and halogen adds to the carbon that has fewer hydrogens.

In hydroboration-oxidation reaction, hydrogen atom gets bonded to the carbon that has fewer hydrogens and the hydroxyl to the carbon that has a greater number of hydrogens. This is a rule opposite of Markovnikov’s addition.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Answer 4

Question

Definition Definition Molecules that have multiple bonds between their carbon atoms. Alkenes are hydrocarbons with a double bond between two adjacent carbon atoms (R 2 C=CR 2 ), whereas alkynes are hydrocarbons with a triple bond between two adjacent carbon atoms R-C=C-R . These two groups are known as unsaturated hydrocarbons. They have fewer hydrogen atoms when compared with alkanes with same number of carbon atoms. The general molecular formula for an unsaturated hydrocarbon can be represented as C n H 2n +2 .

Chapter 8, Problem 31P

Interpretation Introduction