Structural formula of lycopene has to be drawn showing the two sets of four isoprene units linked to form lycopene. Concept Introduction: Terpenes are made by joining five-carbon units, usually in a head to tail-fashion. Isoprene unit: Branched end of isoprene – Head Unbranched end of isoprene - Tail

Question

Many naturally occurring substances contain several carbon–carbon double bonds: some isolated, some conjugated, and some cumulated. Identify the types of carbon–carbon double bonds found in each of the following substances:

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 5, Problem 5.30P

(a)

Interpretation Introduction

Interpretation:

Structural formula of lycopene has to be drawn showing the two sets of four isoprene units linked to form lycopene.

Concept Introduction:

Terpenes are made by joining five-carbon units, usually in a head to tail-fashion.

Isoprene unit:

Branched end of isoprene – Head

Unbranched end of isoprene - Tail

(b)

Interpretation Introduction

Interpretation:

Number of double in lycopene that has a possibility of cis, trans isomerism has to be given and the double bond that shows cis and that shows trans isomers has to be identified.

Concept Introduction:

Terpenes are made by joining five-carbon units, usually in a head to tail-fashion.

Isoprene unit:

Branched end of isoprene – Head

Unbranched end of isoprene - Tail

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

• Trans configuration: In trans configuration, carbon atoms present in the main chain are placed on opposite sides of the carbon-carbon double bond.

• Cis configuration: In cis configuration, carbon atoms present in the main chain are placed on same sides of the carbon-carbon double bond.

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Many naturally occurring substances contain several carbon–carbon double bonds: some isolated, some conjugated, and some cumulated. Identify the types of carbon–carbon double bonds found in each of the following substances:

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Citronellol ((3R)-3,7-dimethyloct-6-en-1-ol, C10H20O) is an organic fragrance found in the oil extracted from lemon grass. a) Name the two functional groups present in the molecule. b) When a few drops of bromine dissolved in hexane is added to a sample of citronellol the brown colour of the bromine rapidly disappears. i. What type of chemical reaction has occurred? ii. Draw the structure of the product formed. iii. Name the product. c) The product formed when citronellol is heated with a mixture of potassium dichromate and sulfuric acid gives a yellow/orange precipitate when shaken with Brady’s reagent (2,4-dinitrophenylhydrazine). It also shows a positive result with Fehling’s solution. i. What type of chemical reaction has occurred ? ii. What type of functional group is present in the product? d) Explain the type of stereoisomerism which may occur in citronellol.

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 5, Problem 5.30P

(a)

Interpretation Introduction

Interpretation:

Structural formula of lycopene has to be drawn showing the two sets of four isoprene units linked to form lycopene.

Concept Introduction:

Terpenes are made by joining five-carbon units, usually in a head to tail-fashion.

Isoprene unit:

Branched end of isoprene – Head

Unbranched end of isoprene - Tail

(b)

Interpretation Introduction

Interpretation:

Number of double in lycopene that has a possibility of cis, trans isomerism has to be given and the double bond that shows cis and that shows trans isomers has to be identified.

Concept Introduction:

Terpenes are made by joining five-carbon units, usually in a head to tail-fashion.

Isoprene unit:

Branched end of isoprene – Head

Unbranched end of isoprene - Tail

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

• Trans configuration: In trans configuration, carbon atoms present in the main chain are placed on opposite sides of the carbon-carbon double bond.

• Cis configuration: In cis configuration, carbon atoms present in the main chain are placed on same sides of the carbon-carbon double bond.

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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 5, Problem 5.30P

(a)

Interpretation Introduction

Interpretation:

Structural formula of lycopene has to be drawn showing the two sets of four isoprene units linked to form lycopene.

Concept Introduction:

Terpenes are made by joining five-carbon units, usually in a head to tail-fashion.

Isoprene unit:

Branched end of isoprene – Head

Unbranched end of isoprene - Tail

(b)

Interpretation Introduction

Interpretation:

Number of double in lycopene that has a possibility of cis, trans isomerism has to be given and the double bond that shows cis and that shows trans isomers has to be identified.

Concept Introduction:

Terpenes are made by joining five-carbon units, usually in a head to tail-fashion.

Isoprene unit:

Branched end of isoprene – Head

Unbranched end of isoprene - Tail

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

• Trans configuration: In trans configuration, carbon atoms present in the main chain are placed on opposite sides of the carbon-carbon double bond.

• Cis configuration: In cis configuration, carbon atoms present in the main chain are placed on same sides of the carbon-carbon double bond.

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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 5, Problem 5.30P

(a)

Interpretation Introduction