The structure of the major stereoisomer formed in the reaction of 3-buten-2-ol with peroxy acid is to be given. The relationship between the two isomers is to be established. The fact whether the two stereoisomers are enantiomers or diastereomers of each is to be specified. The four stereoisomeric products that are formed when racemic 3-buten-2-ol undergo epoxidation is to be given along with their relative amounts. Concept Introduction: > Alkenes are unsaturated hydrocarbons that react with substances that add to the double bond in an addition reaction. Catalytic addition is a syn addition of hydrogen atoms to the carbon-carbon double bond. > In epoxidation of alkenes, peroxyacids transfer oxygen to the double bond of alkenes to form a three membered oxygen containing ring called as epoxides . Addition is stereospecific and syn. A commonly used peroxyacid is peroxyacetic acid. > Peroxyacid prefers to attack the less sterically hindered face of the double bond in orderto form corresponding epoxides. > Diastereomers are the non-mirror images of each other having opposite absolute configuration at only one chiral carbon atom.

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Answer 1

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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 38P

Interpretation Introduction

Interpretation:

The structure of the major stereoisomer formed in the reaction of 3-buten-2-ol with peroxy acid is to be given. The relationship between the two isomers is to be established. The fact whether the two stereoisomers are enantiomers or diastereomers of each is to be specified. The four stereoisomeric products that are formed when racemic 3-buten-2-ol undergo epoxidation is to be given along with their relative amounts.

Concept Introduction:
>
Alkenes are unsaturated hydrocarbons that react with substances that add to the double bond in an addition reaction. Catalytic addition is a syn addition of hydrogen atoms to the carbon-carbon double bond.
>
In epoxidation of alkenes, peroxyacids transfer oxygen to the double bond of alkenes to form a three membered oxygen containing ring called as epoxides. Addition is stereospecific and syn. A commonly used peroxyacid is peroxyacetic acid.
>
Peroxyacid prefers to attack the less sterically hindered face of the double bond in orderto form corresponding epoxides.
>
Diastereomers are the non-mirror images of each other having opposite absolute configuration at only one chiral carbon atom.

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(a) What product(s) are formed when the E isomer of C6H5CH = CHC6H5 is treated with Br2, followed by one equivalent of KOH? Label the resulting alkene(s) as E or Z. (b) What product(s) are formed when the Z isomer of C6H5CH = CHC6H5 is subjected to the same reaction sequence? (c) How are the compounds in parts (a) and (b) related to each other?

Draw the structure of an alkyl bromide with molecular formula CgH13Br that fits each description: (a) a 1° alkyl bromide with one stereogenic center; (b) a 2° alkyl bromide with two stereogenic centers; (c) an achiral 3° alkyl bromide.

Draw all of the substitution and elimination products formed from the given alkyl halide with each reagent: (a) CH3OH; (b) KOH. Indicate the stereochemistry around the stereogenic centers present in the products, as well as the mechanism by which each product is formed.

Answer 2

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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 38P

Interpretation Introduction

Interpretation:

The structure of the major stereoisomer formed in the reaction of 3-buten-2-ol with peroxy acid is to be given. The relationship between the two isomers is to be established. The fact whether the two stereoisomers are enantiomers or diastereomers of each is to be specified. The four stereoisomeric products that are formed when racemic 3-buten-2-ol undergo epoxidation is to be given along with their relative amounts.

Concept Introduction:
>
Alkenes are unsaturated hydrocarbons that react with substances that add to the double bond in an addition reaction. Catalytic addition is a syn addition of hydrogen atoms to the carbon-carbon double bond.
>
In epoxidation of alkenes, peroxyacids transfer oxygen to the double bond of alkenes to form a three membered oxygen containing ring called as epoxides. Addition is stereospecific and syn. A commonly used peroxyacid is peroxyacetic acid.
>
Peroxyacid prefers to attack the less sterically hindered face of the double bond in orderto form corresponding epoxides.
>
Diastereomers are the non-mirror images of each other having opposite absolute configuration at only one chiral carbon atom.

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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 38P

Interpretation Introduction

Interpretation:

The structure of the major stereoisomer formed in the reaction of 3-buten-2-ol with peroxy acid is to be given. The relationship between the two isomers is to be established. The fact whether the two stereoisomers are enantiomers or diastereomers of each is to be specified. The four stereoisomeric products that are formed when racemic 3-buten-2-ol undergo epoxidation is to be given along with their relative amounts.

Concept Introduction:
>
Alkenes are unsaturated hydrocarbons that react with substances that add to the double bond in an addition reaction. Catalytic addition is a syn addition of hydrogen atoms to the carbon-carbon double bond.
>
In epoxidation of alkenes, peroxyacids transfer oxygen to the double bond of alkenes to form a three membered oxygen containing ring called as epoxides. Addition is stereospecific and syn. A commonly used peroxyacid is peroxyacetic acid.
>
Peroxyacid prefers to attack the less sterically hindered face of the double bond in orderto form corresponding epoxides.
>
Diastereomers are the non-mirror images of each other having opposite absolute configuration at only one chiral carbon atom.

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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 38P

Interpretation Introduction