Functional Groups Recap

Carboxylic Acid Alkene Alcohol Ketone

Alkene Halogenoalkane Carboxylic Acid AND Ketone Amine

Halogenoalkane Alkane Aldehyde Aldehyde and Alkene

Aldehyde Aldehyde Ketone Carboxylic Acid

Organic Nomenclature Practice

(a) Pentan-1-ol (b) Hex-2-ene

(c) Propanoic Acid (d) Pentanoic Acid

(e) Hexanal (f) Propanal

(g) Propanone (h) 3-methylbutan-2-one

 (i) 2-methylpentanal (j) 3-hydroxybutanoic acid

(k) Butan-3-on-anoic acid/3-oxobutanoic acid (l) 2-iodobutane

(m) Aminoethane/Ethylamine (n) 3-bromopentane

CH3CH2CH2OH CH3COCH2CH3
(o) Propan-1-ol (p) Butan-2-one (Butanone is fine)
CH3CH(CH3)CH2NH2 CH3CHCHCH(Cl)CH3
(q) 2-methylpropylamine OR 2-amino-2- (r) 2-chloropent-3-ene
methylpropane

Isomers
Questio Answer
n
3

and
4 Yes, chain isomerism
5 Position Isomerism
6 C5H12O
7

8
9 34 electrons
10  Pentan-2-ol would have the higher boiling point.
 Both have the same number of electrons so the strength of the London Forces within
both molecules would be the same.
 However Pentan-2-ol would exhibit hydrogen bonding
 This is the strongest type of intermolecular force and would require the most energy
to overcome the intermolecular forces between molecules.
11 Pentan-2-one
12  Acidified Potassium Dichromate.
 Will turn from orange to green in the presence of F as it’s oxidised.
 Will remain orange in the presence of E
 Fehling’s solution
 Will turn from blue to red in the presence of F.
 Will remain blue in E.
 Tollen’s Reagent
 Will turn from colourless to silver in the presence of F.
 Will remain colourless in E.
13

E-Z Isomerism
Questio Answer
n
14a

b  Restricted rotation about the C=C double bond.

 Differing groups of atoms/atoms bonded to the carbon on each end of the double
bond.
c

d As But-1-ene has the same atoms bonded to one of the carbons in the C=C double bond.
e 2-Bromobutane
f

g The secondary carbocation has a greater stability than the primary carbocation.
So would exist for longer in solution than the primary carbocation.
To therefore be attacked by the positive ions formed from the attacked electrophile.
h

i  Bromine atoms
 They have a greater atomic numbers than the hydrogen atoms.
15
16a

d
e

g
h

i
j

k
l

Optical Isomerism and Chirality

Questio Answer
n
17

18

19

20 Dichloromethane (CCl2H2) does not have four differing groups of atoms bonded to the central
carbon atom.
21/22

23

24 2-bromo-2-chloropropane
25 No, as it has multiple CH3 groups bonded to the central carbon.
26
27 As it contains two functional groups.
28

29

30  As the molecule can form multiple hydrogen bonds per molecule.

 Hydrogen bonds are the strongest type of intermolecular force.
 They require the most energy to separate molecules.
 Therefore this molecule would have a higher boiling point as it would require more
energy than a comparative covalent molecule that has only London Forces between
it’s molecules.
31

32a Z
b Y
c X and Y
33 B

Optical Isomerism and Polarised Light

Questio Answer
n
34 A chiral molecule refers to a molecule that cannot be superimposed on it’s mirror image.

35  Sour milk is not optically active and has no effect on plane polarised light despite
containing a chiral molecule (2-hydroxypropanoic acid).
 Therefore it must be comprised of a equal amounts of both enantiomers.
36 No, as the 2-hydroxypropanoic acid found in muscles is optically active, so must contain an
uneven concentration of both enantiomers.
37 That the mixture contains a greater concentration of the – enantiomer as it rotates light in the
opposite direction.
38 But-1-ene
39 Addition reactions
40 Major: 2-bromobutane
Minor: 1-bromobutane
41

42 2-bromobutane
43

44 That the composition of the 2-enantiomers is equimolar as the solution is not optically active.
45 That the composition of the products is different and has a greater concentration of the major
product which is optically active – 2-Bromobutane.

Optical Isomerism and Reaction Mechanisms

Questio Answer
n
46 When a molecule is chiral and therefore has an effect on plane polarised light.
47 A solution containing a 50:50 mixture of two differing enantiomers
48 As due to the 50:50 split of enantiomers.
Both enantiomers will rotate plane polarised light in one specific direction and therefore
cancel each other out.
49a

b Tertiary
c SN1 reaction mechanism
d  3-bromo-3-methylhexane can form a tertiary carbocation intermediary.
 Tertiary carbocations are the most stable of the different forms, so therefore can react
through the SN1 mechanism.
e  As the solution form would be a racemic mixture.
 With equimolar quantities of each enantiomer formed.
 So therefore there would be no effect on plane polarised light.
f That there is NOT a 50:50 split between the concentrations of the enantiomers and one
enantiomer must have formed in a greater concentration than the other
g

h Amines
i

j  Yes
 As it reacts through the SN1 mechanism, the rate determining step is unimolecular.
 The reaction is first order with respect to the halogenoalkane.
 So this would be the only substance that appears in the rate determining step.

50 SN2
51 CH3CH2CH2CH2Br + OH- → CH3CH2CH2CH2OH + Br-
52
53 Would not be optically active as there is no carbon with four differing groups of atoms around
it.
54
55a  Carbon atoms are not displayed in a skeletal formula.
 Hydrogen atoms are not displayed in a skeletal formula unless bonded to a non-C
atom.
b

c C6H13NO2
d 2-amino-3-methylpentanoic acid.
e As it contains two functional groups (Amine and Carboxylic Acid)
f  Plane-polarised light would be rotated by isoleucine.
 As it contains a chiral carbon (the second carbon)
 Therefore it exists as two differing enantiomers.
g

56a Alkene and Alcohol

b Molecules with the same molecular and structural formula but a different arrangement of
atoms in space.
c E-Z Isomerism
d  Restricted rotation about the C=C double bond.
  Differing groups of atoms/atoms bonded to the carbon on each end of the
double bond.
e  The double bond on the left does not give rise to stereoisomerism as it has two of the
same groups (methyl/CH3) attached to one of the carbons in the double bond.
57a

d
 Carbonyl Compounds
Questio Answer
n
58
Systematic Name Structural Formula Displayed Formula Skeletal Formula

Propanone CH3COCH3

Butanal
CH3CH2CH2CHO
 3-methylpentanal CH3CH2CH(CH3)CH2CHO

3-methylbutan-2-one CH3CH(CH3)COCH3

CH3CH2CH2CH2CH2CHO
Hexanal

Cyclopentanone COCH2CH2CH2CH2

1-bromo-2- CH3CH2CH2COCH(CH3)CH2
methylhexan-3-one Br

The Carbonyl Compounds: Physical Properties

Questio Answer
n
59 Sigma and Pi Bonds
60 Sigma and Pi Bonds
61  C=C bond is comprised of bonds between atoms which are the same.
 So there is no electronegativity difference between the two Carbon atoms.
 The C (2.5) and O (3.5) atoms have differing electronegativity values.
 This gives a Pauling Scale difference of 1.0
 Therefore this means that the C=O bond is polar.
62 London Forces
63 Permanent Dipole – Permanent Dipole Forces and London Forces
64a
b  Propane: 44 (26 electrons)
 Propene: 42 (24 electrons)
 Propanal: 58 (32 electrons)
 Propanone: 58 (32 electrons)
 Propan-1-ol: 60 (34 electrons)
 2-Chloropropane: 78.5 (42 electrons)
c  Propanone and Propanal exhibit permanent dipole-permanent dipole (pd-pd) forces
and London Forces between adjacent molecules.
 Propane and Propene only exhibit London Forces.
 In addition propanone and propanal have more electrons so will have stronger
London Forces.
 So overall more energy is needed to overcome the intermolecular forces in
Propanone and Propanal than in Propene and Propane
d  Both propene and propane only exhibit London Forces between their molecules.
 Propene has less electrons than Propane.
 Therefore the strength of the London Forces in Propene is lower than those in
Propane.
 So less energy is needed to overcome these intermolecular forces and therefore the
boiling point is lower.

E  Propan-1-ol exhibits hydrogen bonding (in addition to London Forces) whilst the
carbonyl compounds (Propanone and Propanal) only exhibit permanent dipole-
permanent dipole (pd-pd) forces and London Forces between adjacent molecules.
 Hydrogen Bonds are the strongest form of intermolecular forces.
 So despite similar molecular masses, and similar strength of London Forces.
 More energy is needed to overcome the intermolecular forces in Propan-1-ol than
those in the carbonyl compounds, so therefore it has a higher boiling point.
f  The electronegativity difference between carbon and oxygen is 1.00
 The electronegativity difference between carbon and chlorine is 0.5
 The carbon-oxygen bond is more polar than the carbon-chlorine bond.
 So therefore stronger permanent dipole-permanent dipole can form in carbonyl
compounds than in 1-chloropropane.
 So more energy needed to overcome the pd-pd attractions in carbonyl compounds so
they have a higher boiling point.
65

66  As the alkyl chain cannot form any hydrogen bonds with water molecules and
therefore the longer the alkyl chain the lower the solubility.

The Carbonyl Compounds: Reactivity

Questio Answer
n
67 Nucleophiles.
68 Nucleophilic Substitution
69  There are a limited number of atoms that can form double bonds with the carbon
atom.
 Would require the addition of a hydrogen atom to ensure the carbon has four bonds.

Reactions of Carbonyl Group

Questio Answer
n
70a CH3CHO + [O] → CH3COOH + H2O
b CH3CH(OH)CH3 + [O] → CH3COCH3 + H2O
c As the carbonyl carbon is not bonded to any hydrogen atoms.
d CH3COCH2CH3 + 2[H] → CH3CH(OH)CH2CH3
e CH3CH2COCH3 + 3I2 + 4NaOH → CHI3 + CH3CH2COONa + 3NaI + 3H2O
f CH3CH2CH2CH2CHO + 2[H] → CH3CH2CH2CH2CH2OH
71a A: Tertiary
B: Secondary
b 2-methylpropan-2-ol
c Alcohol C will oxidise: Aldehyde Structural Formula: CH3CH2CH2CHO
 Alcohol D will oxidise: Aldehyde Structural Formula: CH3CH(CH3)CHO
d Reagent: Acidified Potassium Dichromate
Conditions: Warm Gently and Distil product out.
e Removal of water (2 Hydrogens and one oxygen atom) from a molecule
f Alkenes
g Reagent: Concentrated Phosphoric Acid
Conditions: Heat under reflux at 150-200oC
h C: Structure for But-1-ene. CH3CH2CHCH2
72a Will change from colourless to silver.
b HOCH2COOH
c Heated under reflux would cause formation of a dicarboxylic acid
HOCH2CHO + 3[O] → HOOC-COOH + 3H2O
d HOCH2CH2OH
e There is not a methyl group next to the carbonyl carbon.
73a

b  Heat with Tollen’s Reagent

 To Give a Silver Mirror/Precipitate
c As aldehydes can undergo oxidation but ketones cannot.
d CH3CH=CHCH2OH
e Reduction
f C4H6O + 5O2 → 4CO2 + 3H2O
74a CH3CH2CH2CH2OH + [O] → CH3CH2CH2CHO + H2O
Colour Change: Orange to Green
b Reagent: Tollent’s Reagent or Fehling’s Solution.
Observation with Butan-1-ol: Silver Mirror Forms from colourless
solution or Solution turns Red from Blue
Observation with Butan-2-ol: No reaction
c

Isomer 1: 2-methylpropan-1-ol | Isomer 2: 2-methylpropan-2-ol

 Nucleophilic Addition Reaction Questions
Questio Answer
n
76a Will change from colourless to silver.
B HOCH2COOH
C Heated under reflux would cause formation of a dicarboxylic acid
HOCH2CHO + 3[O] → HOOC-COOH + 3H2O
D HOCH2CH2OH
E

F There is not a methyl group next to the carbonyl carbon.

77a

C Electron pair donor

d  Electron pair in the hydrogen ion are attacking the electron deficient carbon and
forming a dative covalent bond.
 Electrons in the pi bond in the C=O bond are moving to the electronegative oxygen
atom.
 This electron pair is now on the O- atom
78a

b As the functional group within diphenylethanedione is a ketone.

c C14H10O2 + 4[H] → C14H14O2
79a
b

e
80a Aldehyde
Halogenoalkane
b

d
 Optical Isomerism and 2,4-DNP
Questio Answer
n
81a  A chiral molecule is non-superimposable on it’s mirror image.
 2-hydroxypropanoic acid has a carbon atom which is asymmetric/has four different
groups attached.
 Middle carbon labelled in any clear way.


b  2-hydroxypropanoic acid formed in muscle is a single enantiomer or unequal mixture
of enantiomers.
 2-hydroxypropanoic acid formed in milk is a racemic mixture or equimolar mixture of
two enantiomers.
c  1st Step Reagent: NaOH(aq) or KOH(aq)
 2nd step reagent: HCl(aq) or H2SO4(aq)
d  A racemic mixture is not formed/more of one enantiomer is formed/only one
enantiomer is formed.
 Some of the reaction must occur via the SN2 mechanism.
 Nucleophile (OH-) only attacks from one side of the molecules which is opposite to
the side of the leaving group.
e Nucleophilic Addition
f Cyanide Ion/CN-
g

h  Racemic mixture is formed.

 CHO/aldehyde group is planar.
 Cyanide ion attacks from both above or below the molecule.
 Results in equimolar concentrations of each enantiomer.
I  Any value/range with 3750 – 2500cm-1 due to the OH bond which ethanal does not
contain.
j  Q is due to the C=O bond.
 The C=O bond in aldehyde has a range of 1740 – 1720cm-1 and the C=O bond in a
carboxylic acid has a range of 1725-1700cm-1.
 So the peaks cannot be used to distinguish between these two compounds because
they overlap and covers both ranges.
k
81a  Glutamic acid has a carbon atom which is asymmetric/has four different groups
attached.
b

c By the directions in which they rotate plane polarised light.

82a  Ensure that the [H+] and [propanone] is constant or do not affect the rate.
 Only the [I2] changes.
 So that the overall order of the reaction is not determined.
 Otherwise the graph produce would be a curve.
b  Double the concentration of propanone.
 The slope/gradient of the line should also double.

 Monitor/measure the [propanone] over time.

 Plot a [propanone] vs. time graph and calculate half life. Should be constant.
c  I2 not involved in rate-determining step as it doesn’t feature in the rate equation.
 So there must be another faster step where I2 is involved.
 So there must be at least two steps in the reaction mechanism.
d NaHCO3(aq) + HCl(aq) → NaCl(aq) + H2O(l) + CO2(g)
Na+(aq) + HCO3-(aq) + H+(aq) + Cl-(aq) → Na+(aq) + Cl-(aq) + H2O(l) + CO2(g)
Na+(aq) + HCO3-(aq) + H+(aq) + Cl-(aq) → Na+(aq) + Cl-(aq) + H2O(l) + CO2(g)
Answer: HCO3-(aq) + H+(aq) → H2O(l) + CO2(g)
e CH3COCH3 + 3I2 + 4NaOH → CHI3 + CH3COONa + 3NaI + 3H2O.
f
g There is no methyl group next to the carbonyl carbon.

Carboxylic Acids: Nomenclature

Systematic Name Structural Formula Displayed Formula Skeletal Formula

CH3CH2CH2COOH
Butanoic Acid

4-
methylpentanoic CH3CH(CH3)CH2CH2COOH
acid

2-bromo-3- CH3CH(CH3)CH(Br)COOH
methylbutanoic acid

2-
methylpentanoic CH3CH2CH2CH(CH3)COOH
acid

Propanedioic acid HOOCCH2COOH

Carboxylic Acids: Physical Properties

Questio Answer
n
84a

b 2-hydroxypropanenitrile
c 2-hydroxypropanoic acid
d They both have a carbon atom which is asymmetric/has four different groups attached.
e a = 109.5o
b = 104.5o
c = 120o
f Propan-1-ol
g  Lactic acid contains the carboxyl and hydroxyl groups.
 Propan-1-ol only contains the hydroxyl groups.
 Therefore Lactic acid can form more hydrogen bonds per molecule than Propan-1-ol
 This greater number of hydrogen bonds means more energy is needed to separate
adjacent molecules.
 This increased energy requirement results in a higher boiling point.
h  Due to the greater number of hydrogen bonds than can be formed per molecule in
lactic acid.
 This means that more water molecules can form hydrogen bonds with lactic-acid per
molecule than propan-1-ol.
 So with more water molecules hydrating the organic molecule, this results in an
increased solubility.
i

85a  An molecule which only partially ionises when in solution.

b Using a pH probe/meter/data logger
c 0.11 mol dm-3

d @pH4.2 = 6.3 x 10-5 mol dm-3

e Brilliant Yellow
Vertical section or Rapid pH changes should match the pH Range of the indicator.
86a C4H6O6
b C2H3O3
c 2,3-dihydroxybutanedioic acid
d Liquid
e

this is wrong I will edit this!

f  Tartaric acid contains 2 carboxyl and 2 hydroxyl groups.
 2,3-dihydroxybutanoic acid only contains 2 hydroxyl group and 1 carboxyl group
 Therefore Tartaric acid can form more hydrogen bonds per molecule than 2,3-
dihydroxybutanoic acid
 So with more water molecules hydrating the organic molecule, this results in an
increased solubility.
g  Carboxyl groups ionise more readily than hydroxyl groups as the negative charge can
be stabilised across the group.
 The tartaric acid has more carboxyl groups per molecule than 2,3-dihydroxybutanoic
acid.
 Therefore it can ionises more readily, and act as a stronger acid.

Reactions of Carboxylic Acids

Questio Answer
n
87a Neutralisation Reaction
b Redox Reaction
c 2C3H6O3 + 2Mg → 2C3H5O3-Mg+ + H2
d
e C3H5O3Mg
f CH3CH(OH)COOH + CH3CH2OH → CH3CH(OH)COOCH2CH3 + H2O
g

89a As old stocks of aldehydes have oxidised to form carboxylic acids and therefore the
carboxylic acid formed will react with sodium carbonate.
b A larger volume of sodium carbonate solution is neutralized OR a larger volume of
carbon dioxide forms OR faster reaction/more effervescence / more vigorous
c Na2CO3(aq) + 2CH3CH2CH2COOH(aq) → 2CH3CH2CH2COO-Na+(aq) + H2O(l) + CO2(g)
d 3200cm-1 to 2500cm-1 for O-H bond in carboxylic acids
1725cm-1 to 1700cm-1 for C=O bond in carboxylic acids.
e

f Misty fumes would be formed.

g CH3CH2CH2COCl – Butanoyl Chloride
h Butan-1-ol
i Dry Ether
j Reduction, as the carboxylic acid is gaining hydrogen atoms and losing an oxygen atom.
k  Heating under reflux
 Use of concentrated sulfuric acid as a catalyst.
l

88a Methyl Propanoate

b

90
 Esters and Acyl Chlorides: Nomenclature
90. Complete the table below:
Systematic Structural Formula Displayed Formula Skeletal Formula
Name

CH3CH2OCOCH3
Ethyl Ethanoate

2-methylpropyl
CH3CH(CH3)COCl
Chloride.

2-bromobutanoyl
CH3CH2CH(Br)COCl
chloride

Ethyl Propanoate CH3CH2OCOCH2CH3

Ethanoyl
CH3COCl
Chloride

2-methylpropyl
CH3CH(CH3)OCOCH3
ethanoate

Reactions of Acyl Chlorides

Questio Answer
n
91a

b Butanoyl Chloride
c  London Forces and Permanent Dipole – Permanent Dipole forces.
 Esters would have a lower boiling point than a comparable alcohol.
 Esters cannot form hydrogen bonds between adjacent molecules like carboxylic acids
can.
 Therefore not as much energy is required to overcome the intermolecular forces
between Ester molecules.
 So they would have a lower boiling point.
d CH3CH2CH2COCl + H2O(l) → CH3CH2CH2COOH + HCl(g)
92a

b Phosphorus(V) Chloride
c Concentrated Ammonia
d

f
 Hydrolysis of Esters
Questio Answer
n
93 Butanoic Acid – CH3CH2CH2COOH
Propanol – CH3CH2CH2OH
94 Ethanol - CH3CH2OH
Propanoate Ion - CH3CH2COO-
95 Heat under reflux.
Remove products during formation.
96 As the reaction goes to completion and is not reversible like the acidic hydrolysis.
97a Ethyl 3-bromopropanoate
b

and
c

and
d Hydrolysis Reactions
e 2-methylpropanal + [O] → 2-methylpropanoic acid
Conditions: Heat under reflux
Reagent: Acidified Potassium Dichromate.
2-methylpropanoic acid + Methanol → Ester C
Conditions: Heat under reflux
Reagent: Excess Concentrated Sulfuric Acid