IUPAC name of the given alkene has to be given and the configuration has to be specified by the E, Z system. Concept Introduction: IUPAC nomenclature : • Name the main chain: Find the longest carbon chain and name the chain according to the number of carbon atoms it contains; is also the suffix part of the name. • Number the carbon atoms in the main chain: The carbons are numbered, in which the substituents must get lowest possible numbers. • Identify the substituents, and number each: The number at where substituents are present has to be noted. The substituents written as prefix. • Write the names as a single word: Use the hyphen to separate the numbers from the different prefix; commas to separate numbers. If two or more different substituents are present, arrange them in alphabetical order. If two or more identical substituents are present, use prefixes di-, tri-, tetra-, but this particular prefix should not be used for alphabetizing purpose. Alkene: Unsaturated hydrocarbons having at least one double bond between two carbon atoms are known as alkenes . The systematic name of alkenes are written by replacing “ane” of alkane with the suffix name “ene”. Numbering of the main chain should be in such away that alkene group must get lowest possible numbers. E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the bond. Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the bond.

Question

Plan the synthesis of the following compound using the starting material provided and any other reagents needed as long as carbon based reagents have 3 carbons or less. Either the retrosynthesis or the forward synthesis (mechanisms are not required but will be graded if provided) will be accepted if all necessary reagents and intermediates are shown (solvents and temperature requirements are not needed unless specifically involved in the reaction, i.e. DMSO in the Swem oxidation or heat in the KMnO4 oxidation). There may be more than one correct answer, and chemically correct steps will be accepted. Extra points will be given if correct names are provided. The points earned here will be applied to your lowest exam score! H H

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 5.2, Problem 5.5P

(a)

Interpretation Introduction

Interpretation:

IUPAC name of the given alkene has to be given and the configuration has to be specified by the E, Z system.

Concept Introduction:

IUPAC nomenclature:

• Name the main chain: Find the longest carbon chain and name the chain according to the number of carbon atoms it contains; is also the suffix part of the name.

• Number the carbon atoms in the main chain: The carbons are numbered, in which the substituents must get lowest possible numbers.

• Identify the substituents, and number each: The number at where substituents are present has to be noted. The substituents written as prefix.

• Write the names as a single word: Use the hyphen to separate the numbers from the different prefix; commas to separate numbers. If two or more different substituents are present, arrange them in alphabetical order. If two or more identical substituents are present, use prefixes di-, tri-, tetra-, but this particular prefix should not be used for alphabetizing purpose.

Alkene: Unsaturated hydrocarbons having at least one double bond between two carbon atoms are known as alkenes.

The systematic name of alkenes are written by replacing “ane” of alkane with the suffix name “ene”. Numbering of the main chain should be in such away that alkene group must get lowest possible numbers.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the bond.

(b)

Interpretation Introduction

Interpretation:

IUPAC name of the given alkene has to be given and the configuration has to be specified by the E, Z system.

Concept Introduction:

IUPAC nomenclature:

• Name the main chain: Find the longest carbon chain and name the chain according to the number of carbon atoms it contains; is also the suffix part of the name.

• Number the carbon atoms in the main chain: The carbons are numbered, in which the substituents must get lowest possible numbers.

• Identify the substituents, and number each: The number at where substituents are present has to be noted. The substituents written as prefix.

• Write the names as a single word: Use the hyphen to separate the numbers from the different prefix; commas to separate numbers. If two or more different substituents are present, arrange them in alphabetical order. If two or more identical substituents are present, use prefixes di-, tri-, tetra-, but this particular prefix should not be used for alphabetizing purpose.

Alkene: Unsaturated hydrocarbons having at least one double bond between two carbon atoms are known as alkenes.

The systematic name of alkenes are written by replacing “ane” of alkane with the suffix name “ene”. Numbering of the main chain should be in such away that alkene group must get lowest possible numbers.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the bond.

(c)

Interpretation Introduction

Interpretation:

IUPAC name of the given alkene has to be given and the configuration has to be specified by the E, Z system.

Concept Introduction:

IUPAC nomenclature:

• Name the main chain: Find the longest carbon chain and name the chain according to the number of carbon atoms it contains; is also the suffix part of the name.

• Number the carbon atoms in the main chain: The carbons are numbered, in which the substituents must get lowest possible numbers.

• Identify the substituents, and number each: The number at where substituents are present has to be noted. The substituents written as prefix.

• Write the names as a single word: Use the hyphen to separate the numbers from the different prefix; commas to separate numbers. If two or more different substituents are present, arrange them in alphabetical order. If two or more identical substituents are present, use prefixes di-, tri-, tetra-, but this particular prefix should not be used for alphabetizing purpose.

Alkene: Unsaturated hydrocarbons having at least one double bond between two carbon atoms are known as alkenes.

The systematic name of alkenes are written by replacing “ane” of alkane with the suffix name “ene”. Numbering of the main chain should be in such away that alkene group must get lowest possible numbers.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the bond.

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Plan the synthesis of the following compound using the starting material provided and any other reagents needed as long as carbon based reagents have 3 carbons or less. Either the retrosynthesis or the forward synthesis (mechanisms are not required but will be graded if provided) will be accepted if all necessary reagents and intermediates are shown (solvents and temperature requirements are not needed unless specifically involved in the reaction, i.e. DMSO in the Swem oxidation or heat in the KMnO4 oxidation). There may be more than one correct answer, and chemically correct steps will be accepted. Extra points will be given if correct names are provided. The points earned here will be applied to your lowest exam score! H H

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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 5.2, Problem 5.5P

(a)

Interpretation Introduction

Interpretation:

IUPAC name of the given alkene has to be given and the configuration has to be specified by the E, Z system.

Concept Introduction:

IUPAC nomenclature:

• Name the main chain: Find the longest carbon chain and name the chain according to the number of carbon atoms it contains; is also the suffix part of the name.

• Number the carbon atoms in the main chain: The carbons are numbered, in which the substituents must get lowest possible numbers.

• Identify the substituents, and number each: The number at where substituents are present has to be noted. The substituents written as prefix.

• Write the names as a single word: Use the hyphen to separate the numbers from the different prefix; commas to separate numbers. If two or more different substituents are present, arrange them in alphabetical order. If two or more identical substituents are present, use prefixes di-, tri-, tetra-, but this particular prefix should not be used for alphabetizing purpose.

Alkene: Unsaturated hydrocarbons having at least one double bond between two carbon atoms are known as alkenes.

The systematic name of alkenes are written by replacing “ane” of alkane with the suffix name “ene”. Numbering of the main chain should be in such away that alkene group must get lowest possible numbers.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the bond.

(b)

Interpretation Introduction

Interpretation:

IUPAC name of the given alkene has to be given and the configuration has to be specified by the E, Z system.

Concept Introduction:

IUPAC nomenclature:

• Name the main chain: Find the longest carbon chain and name the chain according to the number of carbon atoms it contains; is also the suffix part of the name.

• Number the carbon atoms in the main chain: The carbons are numbered, in which the substituents must get lowest possible numbers.

• Identify the substituents, and number each: The number at where substituents are present has to be noted. The substituents written as prefix.

• Write the names as a single word: Use the hyphen to separate the numbers from the different prefix; commas to separate numbers. If two or more different substituents are present, arrange them in alphabetical order. If two or more identical substituents are present, use prefixes di-, tri-, tetra-, but this particular prefix should not be used for alphabetizing purpose.

Alkene: Unsaturated hydrocarbons having at least one double bond between two carbon atoms are known as alkenes.

The systematic name of alkenes are written by replacing “ane” of alkane with the suffix name “ene”. Numbering of the main chain should be in such away that alkene group must get lowest possible numbers.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the bond.

(c)

Interpretation Introduction

Interpretation:

IUPAC name of the given alkene has to be given and the configuration has to be specified by the E, Z system.

Concept Introduction:

IUPAC nomenclature:

• Name the main chain: Find the longest carbon chain and name the chain according to the number of carbon atoms it contains; is also the suffix part of the name.

• Number the carbon atoms in the main chain: The carbons are numbered, in which the substituents must get lowest possible numbers.

• Identify the substituents, and number each: The number at where substituents are present has to be noted. The substituents written as prefix.

• Write the names as a single word: Use the hyphen to separate the numbers from the different prefix; commas to separate numbers. If two or more different substituents are present, arrange them in alphabetical order. If two or more identical substituents are present, use prefixes di-, tri-, tetra-, but this particular prefix should not be used for alphabetizing purpose.

Alkene: Unsaturated hydrocarbons having at least one double bond between two carbon atoms are known as alkenes.

The systematic name of alkenes are written by replacing “ane” of alkane with the suffix name “ene”. Numbering of the main chain should be in such away that alkene group must get lowest possible numbers.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the bond.

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Answer 3

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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 5.2, Problem 5.5P

(a)

Interpretation Introduction

Interpretation:

IUPAC name of the given alkene has to be given and the configuration has to be specified by the E, Z system.

Concept Introduction:

IUPAC nomenclature:

• Name the main chain: Find the longest carbon chain and name the chain according to the number of carbon atoms it contains; is also the suffix part of the name.

• Number the carbon atoms in the main chain: The carbons are numbered, in which the substituents must get lowest possible numbers.

• Identify the substituents, and number each: The number at where substituents are present has to be noted. The substituents written as prefix.

• Write the names as a single word: Use the hyphen to separate the numbers from the different prefix; commas to separate numbers. If two or more different substituents are present, arrange them in alphabetical order. If two or more identical substituents are present, use prefixes di-, tri-, tetra-, but this particular prefix should not be used for alphabetizing purpose.

Alkene: Unsaturated hydrocarbons having at least one double bond between two carbon atoms are known as alkenes.

The systematic name of alkenes are written by replacing “ane” of alkane with the suffix name “ene”. Numbering of the main chain should be in such away that alkene group must get lowest possible numbers.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the bond.

(b)

Interpretation Introduction

Interpretation:

IUPAC name of the given alkene has to be given and the configuration has to be specified by the E, Z system.

Concept Introduction:

IUPAC nomenclature:

• Name the main chain: Find the longest carbon chain and name the chain according to the number of carbon atoms it contains; is also the suffix part of the name.

• Number the carbon atoms in the main chain: The carbons are numbered, in which the substituents must get lowest possible numbers.

• Identify the substituents, and number each: The number at where substituents are present has to be noted. The substituents written as prefix.

• Write the names as a single word: Use the hyphen to separate the numbers from the different prefix; commas to separate numbers. If two or more different substituents are present, arrange them in alphabetical order. If two or more identical substituents are present, use prefixes di-, tri-, tetra-, but this particular prefix should not be used for alphabetizing purpose.

Alkene: Unsaturated hydrocarbons having at least one double bond between two carbon atoms are known as alkenes.

The systematic name of alkenes are written by replacing “ane” of alkane with the suffix name “ene”. Numbering of the main chain should be in such away that alkene group must get lowest possible numbers.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the bond.

(c)

Interpretation Introduction

Interpretation:

IUPAC name of the given alkene has to be given and the configuration has to be specified by the E, Z system.

Concept Introduction:

IUPAC nomenclature:

• Name the main chain: Find the longest carbon chain and name the chain according to the number of carbon atoms it contains; is also the suffix part of the name.

• Number the carbon atoms in the main chain: The carbons are numbered, in which the substituents must get lowest possible numbers.

• Identify the substituents, and number each: The number at where substituents are present has to be noted. The substituents written as prefix.

• Write the names as a single word: Use the hyphen to separate the numbers from the different prefix; commas to separate numbers. If two or more different substituents are present, arrange them in alphabetical order. If two or more identical substituents are present, use prefixes di-, tri-, tetra-, but this particular prefix should not be used for alphabetizing purpose.

Alkene: Unsaturated hydrocarbons having at least one double bond between two carbon atoms are known as alkenes.

The systematic name of alkenes are written by replacing “ane” of alkane with the suffix name “ene”. Numbering of the main chain should be in such away that alkene group must get lowest possible numbers.

E configuration: The geometric isomers are given E configuration if high priority groups are placed on opposite sides of the bond.

Z configuration: The geometric isomers are given Z configuration if high priority groups are placed on same sides of the bond.

Expert Solution & Answer

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Answer 4

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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 5.2, Problem 5.5P

(a)

Interpretation Introduction