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NATIONAL QUALIFICATIONS CURRICULUM SUPPORT

Chemistry

Consumer Chemistry

Predicting Physical Properties of

Molecules from Functional Groups

[HIGHER]

2 CONSUMER CHEMISTRY (H, CHEMISTRY)

© Learning and Teaching Scotland 2010

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Acknowledgement

Learning and Teaching Scotland gratefully acknowledges this contribution to the National

Qualifications support programme for Chemistry.


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CONSUMER CHEMISTRY (H, CHEMISTRY) 3


Contents

Introduction 4

Questions 5

Answers 19

INTRODUCTION



Introduction

This resource supports the Consumer Chemistry unit of the revised Higher

Chemistry. The resource has the following purposes:

1. to allow students to become familiar with identifying functional groups

within everyday molecules, some of which have complex structures

2. to enable students to relate intermolecular forces to the functional

groups present

3. to enable students to explain the physical properties of molecules based

on the functional groups present.

QUESTIONS



Questions

Question 1

Benzaldehyde is an aromatic compound with an almond-like smell, which is

used in flavourings and perfumes.

Circle and name the functional group on the benzaldehyde molecule below.

C

H

O

Benzaldehyde

QUESTIONS



Question 2

Cholesterol is an important molecule present in the human body. However,

high levels of a certain type of cholesterol in the blood are linked with

illnesses such as heart disease and strokes.

CH2

CH

CH2

CH2

C

C

CH CH2

CH

CH

CH2CH2

C

CH

CH2

CH2

CH

HO

CH3 CH3

CH

CH3

CH2 CH2 CH2 CH2

Cholesterol

CH3

CH3

(a) Identify the two circled functional groups on the cholesterol molecule .

(b) Explain why this compound has a high boiling point.

QUESTIONS



Question 3

β-carotene is a member of a family of chemicals called the carotenoids. It is responsible for the orange colour in many fruits

and vegetables, including carrots.

CH2

CH2

CH2 C

C

C

CH3

CH3

CH3

CH CH C

CH3

CH CH CH C

CH3

CH CH CH CH C

CH3

CH CH CH C

CH3

CH CH C

C CH2

CH2

CH2C

CH3

CH3

CH3

-carotene

(a) Which functional group is present throughout the structure of β-carotene?

(b) Is the carbon-to-carbon double bond polar or non-polar?

(c) Which type of intermolecular forces will exist between β -carotene molecules?

QUESTIONS



Question 4

The vanilla bean produces a compound called vanillin , which is used as a

flavouring additive in sweet foods such as ice cream.

C

H

O

OH

O CH3

Vanillin

(a) Identify two functional groups present in vanillin.

(b) What is the strongest type of intermolecular force present between

molecules of vanillin?

QUESTIONS



Question 5

The compounds shown below are active ingredients in over -the-counter

drugs. Aspirin is used as an analgesic (to relieve pain) and as an antipyretic

(to reduce elevated body temperatures). Ibuprofen is used as an anti -

inflammatory agent (to counteract swelling or inflammation of the joints, skin

and eyes).

C

OHO

O

C

CH3

O

Aspirin(acetylsalicylic acid)

CH2CH

CH3

C

O

OH

CHCH3

CH3

Ibuprofen

(a) Which functional group is present in both drug molecules?

(b) Which functional group is present in aspirin but not in ibuprofen?

QUESTIONS



Question 6

The two compounds shown below have similar molecular mass.

HO N C

O

CH3

Paracetamol

H

C

CH2

CH

CH2

CH

CO

CH3

C

CH2 CH3

Carvone

Molecular mass = 151 amu Molecular mass = 150 amu

(amu = atomic mass units)

(a) Identify two different types of functional group present in paracetamol.

(b) Identify two different types of functional group present in carvone.

(c) In terms of intermolecular forces, explain why the melting point of

paracetamol (168°C) is significantly higher than that of carvone (25°C).

QUESTIONS



Question 7

Capsaicin and zingerone are natural strong-smelling compounds found in

chilli pepper and ginger, respectively.

CH2 CH2 C

O

CH3

OCH3Zingerone

HO

OCH3

CH2 N C

O

CH2 CH2 CH2 CH2 CH CH CH

CH3

CH3

Capsaicin

HO

H

(a) Identify the two circled functional groups in zingerone.

(b) Identify the three circled functional groups in capsaicin.

QUESTIONS



Question 8

Oil of wintergreen is an essential oil that is used in aromatherapy massage

blends for the joints and muscles. Methyl salicylate is the active ingredient of

oil of wintergreen.

OH

C

O

O

CH3

methyl salicylate

(a) Identify the two circled functional groups present in methyl salicylate.

(b) Explain whether the hydroxyl group contains a polar or a non -polar

bond.

QUESTIONS



Question 9

Lycopene (C40H56) is the red pigment found in tomatoes and other red fruits and vegetables.

CH CH CH C

CH3

CH CH CH C

CH3

CH CH CH CH C

CH3

CH CH CH C

CH3

CH CH CH

Lycopene

C

CH3

CH2 CH2C

CH3

CH2CH2CHC

CH3

H3C CH C

CH3

CH3

Astaxanthin (C40H52O4) is a pink pigment found in salmon, trout, lobster and shrimp.

C

CH

CH2 C

C

C

CH3

CH3

CH CH C

CH3

CH CH CH C

CH3

CH CH CH CH C

CH3

CH CH CH C

CH3

CH CH C

C C

CH

CH2C

CH3

CH3

CH3

Astaxanthin O

OHHO

O CH3

(a) Which functional group is found repeatedly throughout the structure of lycopene?

(b) Name two additional functional groups that are found in the structure of astaxanthin.

(c) Explain why astaxanthin (215°C) has a higher boiling point than lycopene (172°C).

QUESTIONS



Question 10

Tetracycline is an antibiotic that is widely used as an alternative treatment for

patients who are allergic to penicillin. It prevents the growth of invading

bacteria, allowing the body’s own immune system to fight off infection.

C

C

CH

C

C

CH2

CH

C

C

C

C

CH

OH O

HO CH3

OH

OH

O

OH

C

O

N

N

CH3CH3

Tetracycline

H

H

Identify four different types of functional group on the tetracycline structure.

QUESTIONS



Question 11

L-tyrosine is an important building block in the formation of almost all

proteins in the body.

CH

NH2

C

O

OH

HO CH2

L-tyrosine

Identify three functional groups present in its structure.

QUESTIONS



Question 12

Alanine (2-aminopropanoic acid) is found in meat, fish, seafood and dairy

products.

CH

CH3

C

O

OH

N

alanine

H

H

Which functional groups are present in an alanine molecule?

A. Aldehyde, amine and hydroxyl

B. Ketone, amine and hydroxyl

C. Carboxyl and amine

D. Amino acid and hydroxyl

QUESTIONS



Question 13

Aspirin and ibuprofen are common over-the-counter drugs.

C

OHO

O

C

CH3

O


CH2CH

CH3

C

O

OH

CHCH3

CH3

Ibuprofen

Identify the term that can be applied to aspirin but not to ibuprofen.

A. Aldehyde

B. Ketone

C. Carboxylic acid

D. Ester

QUESTIONS



Question 14

Cyclohexyne is used in insect repellents.

cyclohexyne

C

C

C

C

C

C

H H

H

H H

H

H

H

Which of the following would be the best solvent for dissolving cycloh exyne?

A. Hexane

B. Hexanal

C. Hexanol

D. Hexanone

ANSWERS



Answers

Question 1

Benzaldehyde is an aromatic compound with an almond-like smell, which is

used in flavourings and perfumes.

Circle and name the functional group on the benzaldehyde molecule below.

C

H

O

Benzaldehyde

Carbonyl group

ANSWERS



Question 2

Cholesterol is an important molecule present in the human body. However,

high levels of a certain type of cholesterol in the blood are linked with

illnesses such as heart disease and strokes.

CH2

CH

CH2

CH2

C

C

CH CH2

CH

CH

CH2CH2

C

CH

CH2

CH2

CH

HO

CH3 CH3

CH

CH3

CH2 CH2 CH2 CH2

Cholesterol

CH3

CH3

(a) Identify the two circled functional groups on the cholesterol molecule

Hydroxyl group and carbon-to-carbon double bond.

(b) Explain why this compound has a high boiling point.

Hydrogen bonding exists between the polar hydroxyl groups on

cholesterol molecules. Extra energy is required to overcome these

strong intermolecular forces of attraction, and therefore the boiling

point is high.

Additionally, cholesterol is a large molecule containing a large number

of electrons, which leads to relatively strong London forces existing

between cholesterol molecules. As more energy is therefore required to

separate the molecules, the boiling point is higher.

Hydroxyl group

Carbon-to-carbon double bond

ANSWERS



Question 3

β-carotene is a member of a family of chemicals called the carotenoids. It is

responsible for the orange colour in many fruits and vegetables, including

carrots.

CH2

CH2

CH2 C

C

C

CH3

CH3

CH3

CH CH C

CH3

CH CH CH C

CH3

CH CH CH CH C

CH3

CH CH CH C

CH3

CH CH C

C CH2

CH2

CH2C

CH3

CH3

CH3

-carotene

(a) Which functional group is present throughout the struc ture of β-

carotene?

Carbon-to-carbon double bond.

(b) Is the carbon-to-carbon double bond polar or non-polar?

Both atoms have the same electronegativity value (2.5) therefore the

bonds are non-polar covalent.

(c) Which type of intermolecular forces will exis t between β-carotene

molecules?

London dispersion forces as the molecule does not contain polar bonds.

ANSWERS



Question 4

The vanilla bean produces a compound called vanillin , which is used as a

flavouring additive in sweet foods such as ice cream.

C

H

O

OH

O CH3

Vanillin

(a) Identify two functional groups present in vanillin.

Hydroxyl group and carbonyl group (aldehyde) .

(b) What is the strongest type of intermolecular force present between

molecules of vanillin?

Hydrogen bonding due to the presence of hydroxyl groups.

Carbonyl group

(aldehyde)

Hydroxyl group

ANSWERS



Question 5

The compounds shown below are active ingredients in over -the-counter

drugs. Aspirin is used as an analgesic (to relieve pain) and as an antipyretic

(to reduce elevated body temperatures). Ibuprofen is used as an anti-

inflammatory agent (to counteract swelling or inflammation of the joints, skin

and eyes).

C

OHO

O

C

CH3

O


CH2CH

CH3

C

O

OH

CHCH3

CH3

Ibuprofen

(a) Which functional group is present in both drug molecules?

Carboxyl group.

(b) Which functional group is present in aspirin but not in ibuprofen?

Ester link.

Carboxyl group Carboxyl group

Ester link

ANSWERS



Question 6

The two compounds shown below have similar molecular mass.

HO N C

O

CH3

Paracetamol

H

C

CH2

CH

CH2

CH

CO

CH3

C

CH2 CH3

Carvone

Molecular mass = 151 amu Molecular mass = 150 amu

(amu = atomic mass units)

(a) Identify two different types of functional group present in paracetamol.

Hydroxyl group and amide link

(b) Identify two different types of functional group present in carvone.

Carbonyl group and carbon-to-carbon double bond.

(c) In terms of intermolecular forces, explain why the melting point of

paracetamol (168°C) is significantly higher than that of carvone (25°C).

Paracetamol contains the hydroxyl group, therefore hydrogen bonding

exists between its molecules. Permanent dipole–permanent dipole

interactions form between carvone molecules. Hydrogen bonds are an

unusually strong type of permanent dipole–permanent dipole

interactions, so more energy is required to overcome the intermolecular

forces of attraction between paracetamol molecules, and therefore

paracetemol has a higher boiling point than carvone.

Carbon-to-carbon

double bond

Amide link

Hydroxyl group

Carbonyl group

ANSWERS



Question 7

Capsaicin and zingerone are natural strong-smelling compounds found in

chilli pepper and ginger, respectively.

CH2 CH2 C

O

CH3

OCH3Zingerone

HO

OCH3

CH2 N C

O

CH2 CH2 CH2 CH2 CH CH CH

CH3

CH3

Capsaicin

HO

H

(a) Identify the two circled functional groups in zingerone.

Hydroxyl group and carbonyl group.

(b) Identify the three circled functional groups in Capsaicin.

Hydroxyl group, amide link and carbon-to-carbon double bond.

Amide link

Carbon-to-carbon

double bond

Hydroxyl group

Carbonyl group

ANSWERS



Question 8

Oil of wintergreen is an essential oil that is used in aromatherapy massage

blends for the joints and muscles. Methyl salicylate is the active ingredient of

oil of wintergreen.

OH

C

O

O

CH3

methyl salicylate

(a) Identify the two circled functional groups present in methyl salicylate.

Ester link and hydroxyl group.

(b) Explain whether the hydroxyl group contains a polar or a non -polar

bond.

The bond is polar because of the difference in electronegativity between

oxygen (3.5) and hydrogen (2.2).

ANSWERS



Question 9

Lycopene (C40H56) is the red pigment found in tomatoes and other red fruits and vegetables.

CH CH CH C

CH3

CH CH CH C

CH3

CH CH CH CH C

CH3

CH CH CH C

CH3

CH CH CH

Lycopene

C

CH3

CH2 CH2C

CH3

CH2CH2CHC

CH3

H3C CH C

CH3

CH3

Astaxanthin (C40H52O4) is a pink pigment found in salmon, trout, lobs ter and shrimp.

C

CH

CH2 C

C

C

CH3

CH3

CH CH C

CH3

CH CH CH C

CH3

CH CH CH CH C

CH3

CH CH CH C

CH3

CH CH C

C C

CH

CH2C

CH3

CH3

CH3

Astaxanthin O

OHHO

O CH3

(a) Which functional group is found repeatedly throughout the structure of lycopene?

Carbon-to-carbon double bond.

(b) Name two additional functional groups that are found in the structure of astaxanthin.

Carbonyl group (ketone) and hydroxyl group.

(c) Explain why astaxanthin (215°C) has a higher boiling point than lycopene (172°C).

Astaxanthin contains several polar groups and forms hydrogen bonding and other permanent dipole –permanent dipole

attractions between molecules. Lycopene contains no polar bonds, therefore only has London dispersion forces between

molecules. More energy is required to break the stronger attractive forces between astaxanthin molecules, so its boiling

point is higher.

ANSWERS



Question 10

Tetracycline is an antibiotic that is widely used as an alternative treatment for

patients who are allergic to penicillin. It prevents the growth of invading

bacteria, allowing the body’s own immune system to fight off infection.

C

C

CH

C

C

CH2

CH

C

C

C

C

CH

OH O

HO CH3

OH

OH

O

OH

C

O

N

N

CH3CH3

Tetracycline

H

H

Identify four different types of functional group on the tetracycline structure.

Amino group, carbonyl group, hydroxyl group and carbon-to-carbon double

bond.

ANSWERS



Question 11

L-tyrosine is an important building block in the formation of almost all

proteins in the body.

CH

NH2

C

O

OH

HO CH2

L-tyrosine

Identify three functional groups present in its structure.

Amino group, hydroxyl group and carboxyl group.

ANSWERS



Question 12

Alanine (2-aminopropanoic acid) is found in meat, fish, seafood and dairy

products.

CH

CH3

C

O

OH

N

alanine

H

H

Which functional groups are present in an alanine molecule?

A. Aldehyde, amine and hydroxyl

B. Ketone, amine and hydroxyl

C. Carboxyl and amine

D. Amino acid and hydroxyl

ANSWERS



Question 13

Aspirin and ibuprofen are common over-the-counter drugs.

C

OHO

O

C

CH3

O


CH2CH

CH3

C

O

OH

CHCH3

CH3

Ibuprofen

Identify the term that can be applied to aspirin but not to ibuprofen.

A. Aldehyde

B. Ketone

C. Carboxylic acid

D. Ester

ANSWERS



Question 14

Cyclohexyne is used in insect repellents.

cyclohexyne

C

C

C

C

C

C

H H

H

H H

H

H

H

Which of the following would be the best solvent for dissolving cyclohexyne?

A. Hexane

B. Hexanal

C. Hexanol

D. Hexanone

Cyclohexyne is a non-polar molecule, and therefore hexane (a non-polar

solvent) will dissolve it best.

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