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Chemsitry > Organic > Flashcards

Organic Flashcards

1
Q

Why can SN1 molecules form 2 enantioners while sn2 onlt does 1

A

The structure of sn1 allows molecules to attack from both sides, creating two different molecules

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2
Q

What alcohols undergo sn2

A

Primary and secondary

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3
Q

What alcohols undergo sn2

A

Tertiary

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4
Q

Basic formula for chlorination to create Halogenoalkane

A

R-OH + PCl5 becomes R-Cl + POCl3 + HCl

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5
Q

Conditions for chlorination

A

Room temperature

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6
Q

Basic formula for Bromination

A

2KBr + H2SO4 becomes K2SO4 + 2HBr

R-OH + HBr becomes R-Br + H2O

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7
Q

Conditions and reagents for Bromination

A

KBr and 50% concentrated H2SO4

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8
Q

Why is full strength H2SO4 not used in Bromination

A

Would oxidise Br-

50% conc reduces chance of oxidation happening

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9
Q

Basic formula for iodination

A

2P + 3I2 becomes 2PI3

3R-OH + PI3 becomes 3R-I + H3PO3

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10
Q

Conditions and reagents for iodination

A

Red phosphorus and I2

Reflux

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11
Q

What is a nucleophile

A

all have a lone pair and full or partial negative charge

All attracted to areas of positive charge

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12
Q

Regents and conditions for reaction of Aqueous alkali and Halogenoalkane

A

Aqueous alkali

50/50 ethanol/water and reflux

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13
Q

Conditions and reagents Hydrolysis of halogenoalkanes

A

H2O from AgNO3

Ethanol solvent and warm

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14
Q

Appearance of silver halides

A

AgCl white ppt
AgBr cream ppt
AgI yellow ppt

Darker in colour down group

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15
Q

What affects bond reactively for halogenoalkanes

A

Bond strength

Most reactive R-I as weakest bond

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16
Q

Conditions and reagents for reaction of ammonia and Halogenoalkane

A

NH3 solution

Heat in sealed tube

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17
Q

Conditions and reagents of potassium cyanide and halogenoalkanes

A

KCN

In ethanol + heat

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18
Q

Where does OH- attack carbon from in Sn2

A

Attacks from opposite side to halogen

Does so as S- hydrogen on other side will repel OH- ion

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19
Q

Overall equation for Halogenoalkane and NaOH

A

R-X + NaOH becomes R-OH and NaX

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20
Q

Reagents and conditions for Halogenoalkane and NaOH

A

NaOH

Aqueous warm

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21
Q

Overall equation for Halogenoalkane and KCN

A

R—X + KCN becomes R-CN + KX

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22
Q

Reagents and conditions for Halogenoalkane and KCN

A

KCN

Ethanolic, warm

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23
Q

Overall equation for Halogenoalkane and NH3

A

R-X + 2NH3 becomes R-NH2 + NH4X

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24
Q

Conditions and reagents for Halogenoalkane and NH3

A

NH3

Excess conc ammonia dissolved in ethanol under pressure

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25
Q

Reagents and conditions for Halogenoalkane and KOH

A

KOH

Ethanolic, hot

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26
Q

Energy profile for SN2 reaction

A

Rises during formation of transition state

Drops for final product

Overall exothermic

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27
Q

How does hydrogen bonding occur

A

When a hydrogen atom is bonded to a highly electronegative atom (N, O or F) that forms a strong attraction to another highly electronegative atom on another molecule

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28
Q

Basic equation for oxidation of primary alcohol

A

CH3OH + 2[O] becomes H-COOH + H20

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29
Q

How to isolate the aldehyde when oxidising a primary alcohol

A

Set up for distillation and the aldehyde distils before being oxidised

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30
Q

How to isolate the carboxylic acid when oxidising a primary alcohol

A

Reflux first so aldehyde goes into reaction mixture and is oxidised

When reaction complete set up for distillation and distill RCOOH

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31
Q

Basic formula for oxidation of secondary alcohol

A

CH3-CHOH-CH3 + [O] becomes CH3-CO-CH3 + H2O

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32
Q

Why don’t tertiary alcohols oxidise

A

No H available to make H2O

Not energetically favourable

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33
Q

Why do we crack alkanes

A

Shorter alkanes burn more easily, with less volatility and a clearer flame

This makes them useful fuels

Demand for short alkanes is high but supply is low, so we crack alkanes to increase supply of short alkanes

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34
Q

What is knocking and when does it occur

A

Knocking is when hydrocarbons ignite too early

Occurs with a low octane number

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35
Q

What is reforming

A

Where straight chain carbons are rearranged into cyclic alkanes or benzene rings

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36
Q

Reagents and conditions for reforming

A

Platinum and aluminium oxide catalyst

500 degrees C

20 atmospheres

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37
Q

When is carbon monoxide formed in hydrocarbon combustion

A

When there is an insufficient supply of oxygen

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38
Q

What is a free radical

A

A very reactive species that has an unpaired electron

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39
Q

What is homolytic fission

A

When the covalent bond breaks, 1 electron goes to each bonding atom

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40
Q

What is heterolytic fission

A

When one atom gains both bonding electrons

Forms ions

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41
Q

What are the requirements for cis/trans isomerisation to occur

A

Must be no rotation within the molecule (aka a double bond)

Each carbon atom either side of double bond needs two different groups

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42
Q

When is E/Z isomerism used

A

When cis/trans can’t be used

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43
Q

When is an isomer given E notation

A

When the highest atomic number groups on both carbons are on opposite sides

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44
Q

When is an isomer given Z notation

A

When the highest atomic number groups on both carbons are on the same side

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45
Q

When is an isomer given cis notation

A

The heaviest groups on the same side

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46
Q

When is an isomer given trans notation

A

The heaviest groups on opposite sides

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47
Q

Conditions and reagents for reaction of hydrogen and Alkene

A

Alkene and hydrogen

High temperature, nickel catalyst

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48
Q

Conditions and reagents for halogenation of Alkene

A

Alkene and halogen

Room temp

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49
Q

Conditions and reagents to change ethene to ethane

A

Hydrogen
Nickel catalyst
150 degrees C

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50
Q

Conditions and reagents to change ethene to ethanol

A

Steam
H3PO4 catalyst
300-600 degrees C
70 atm

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51
Q

Difference between creating bromethane and dibromoethane from ethene

A

Bromethane uses hydrogen bromine

Dibromoethane uses bromine

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52
Q

What is markovnikovs rule

A

When a hydrogen halide is added to an unsymmetrical Alkene, the hydrogen is attached to the carbon with the most hydrogens already attached

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53
Q

How is Markovnikovs rule used

A

Predicts the minor and major products of a reaction between hydrogen halides and hydrocarbons

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54
Q

Reagent and conditions for oxidation of Alkene

A

Alkene KMnO4 (oxidising agent)

Dilute H2SO4 catalyst

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55
Q

How to test for a carbon- carbon double bond

A

Potassium manganate (VII)
Bromine water

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56
Q

Positive result for C-C double bond potassium manganate

A

Purple/pink to colourless

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57
Q

Positive result for C-C double bond bromine water

A

Decolourises bromine water orange to colourless

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58
Q

Where is a sigma bond found

A

In a region of space between the nuclei of two atoms sharing the electrons

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59
Q

How is a sigma bond held together

A

By the electrostatic attraction between the electrons and the nuclei

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60
Q

Why are pi bonds formed

A

The overlap between two p orbitals leads to pi bonds being formed

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61
Q

Are sigma or pi bonds stronger

A

Sigma

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62
Q

What is necessary for free radicals to be formed

A

UV light

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63
Q

What affects the rate a precipitate is formed when silver nitrate is added to a Halogenoalkane

A

The strength of the C-X bond

Therefore Tertiary is the slowest as the C-X bond is weakest in tertiary alcohols

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64
Q

Reagents to test for alcohols

A

PCl5

K2Cr2O7

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65
Q

Result on positive result for alcohol with PCl5

A

Steamy white fumes

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66
Q

Colour change on positive result for alcohol with K2Cr2O7

A

Orange solution turns green

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67
Q

Why do primary alcohols not undergo SN1 reactions

A

Primary carbocation is less stable than a tertiary carbocation

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68
Q

Test for carbonyl group

A

Brady’s reagent

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69
Q

Test for aldehyde

A

Fehlings solution

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70
Q

Difference between acid hydrolysis and alkali hydrolysis of an ester

A

Acid is a catalyst

Reaction is reversible for acid

Produced carboxylic acid in acid

H+ electrophile for acid

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71
Q

What does LiAlH4 do

A

Converts aldehydes, carboxylic acid and esters to primary alcohols

Converts ketones to secondary alcohols

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72
Q

Positive test for Brady’s reagent

A

Yellow ppt

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73
Q

Positive result for Fehlings test

A

Red ppt

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74
Q

Why are molecules with a benzene ring sparingly soluble in water

A

Because of the London forces because of the rings between the molecules

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75
Q

Reagents and conditions to form ester

A

Heat
Conc H2SO4

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76
Q

What is stereoisomerism

A

Same molecular and structural formula but a different arrangement in space

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77
Q

What is structural isomerism

A

Same molecular formula, different structural formula

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78
Q

What is the property that gives optical isomerism

A

Ability to rotate the plane of polarised light

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79
Q

Which Sn reaction produced a racemic mixture and why

A

SN1
Creates a planar intermediate ion so that the OH- ion can attack from either side
Therefore produces two entaniomers- racemic mixture

80
Q

Why does sn2 only create one enantiomer

A

OH group can only attack from one side, creates an asymmetrical molecule

81
Q

Structure of an aldehyde

A

R-CH=O

82
Q

Structure of a ketone

A

R-CO-R

83
Q

Intermolecular forces in aldehydes and ketones

A

London forces
Permanent dipole

84
Q

Solubility of aldehydes and ketones

A

Small carbonyls soluble in water

As carbon chain gets longer London forces become dominant force, not enough energy to break H bonds in water

85
Q

Conditions and reagents for reduction of carbonyls (ketones and aldehydes)

A

LiAlH4

Dry ether

86
Q

Tollens reagent test

A

Add a drop of NaOH to some AgNO3 to form Tollens reagent, Ag2O
Aldehyde reduces this complex to appear as black ppt or silver mirror

87
Q

How to test for CH3CO
(Include method)

A

Add I2 and NaOH until colour just disappears

Add substance to be tested and heat

Yellow ppt with antiseptic smell formed

88
Q

Reagents and conditions for carbonyl and hydrogen cyanide

A

Excess KCN or NaCN in water
Little H2SO4

Room Temp

89
Q

What type of reaction is HCN and carbonyl

A

Nucleophilic addition

90
Q

What is a chiral centre

A

A carbon atom with 4 groups attached to it

91
Q

What does tollens reagent test for

A

Aldehyde

92
Q

Why is the Kekule structure for benzene incorrect

A

Lack of reactivity of benzene- benzene undergoes subsitution reactions not addition

Thermodynamic stability- benzene is more thermally stable than should be expected

Bond lengths- alternating C-C and C=C bond would have varying lengths

93
Q

What is the Kekule structure

A

A six carbon cyclohydrocarbon with alternating C-C single and C=C double bonds

94
Q

Why does Benzene undergo subsitution reactions

A

Tends to retain delocalised system

95
Q

What type of subsitution reactions does benzene undergo

A

Electrophilic

96
Q

Reagents and conditions for halogenation of benzene

A

Reagents- benzene, halogen

Conditions- halogen carrier catalyst eg AlCl3 or FeBr3
Room temp and pressure

97
Q

Steps in mechanism for halogenation of benzene

A

Generation of electrophile eg Br2 + AlBr3 becomes Br+ and AlBr4-

Benzene reacts with electrophile

Regeneration of catalyst

98
Q

Reagents and conditions for nitration of benzene

A

Reagents- benzene and nitric acid
Conditions- 50 degrees C, conc sulfuric acid

99
Q

What do all friedel-crafts reactions involve

A

Halogen-carrier catalyst

Formation of C-C bond

100
Q

What is alkylation

A

Subsitution of a halogen from the benzene with an alkyl group

101
Q

Reagents and conditions of alkylation of benzene

A

Reagents- benzene and haloalkane

Conditions- halogen carrier catalyst

102
Q

What do friedel-crafts reactions do

A

Increase the length of a carbon chain

103
Q

Conditions and Reagants for acylation

A

Reagents- acyl chloride, benzene

Conditions- halogen-carrier catalyst, reflux

104
Q

Standard equation for alkylation of benzene

A

Benzene and R(alkyl group) becomes C6H5R(eg ethylbenzene) and HCl

105
Q

Standard reaction for acylation

A

Benzene and R-COOH becomes Benzene attached to a COR and H+

106
Q

What is a phenol

A

A phenol is a an organic compound with a benzene ring with an -OH group attached
The oxygen must be directly bonded to a carbon in the ring

107
Q

What is the use of alkyl phenols

A

Detergents

108
Q

What is the use of chlorophenols

A

Antiseptics

109
Q

Properties of phenol

A

Phenol is solid under standard conditions
It is a slightly soluble in water due to hydrogen bonding between OH groups
The large, non-polar benzene ring decreases its solubility

110
Q

Why is phenol a solid at RT and benzene a liquid

A

Phenol has H bonding while benzene only has london forces
H bonding are stronger and thus require more energy to overcome

111
Q

Why is phenol slightly soluble in water while benzene is immiscible

A

The OH of phenol can form hydrogen bonds with water
Non polar benzene ring reduces solubility

112
Q

Why is phenol highly soluble in NaOH while benzene is immiscible

A

Phenol reacts with NaOH
Products of neutralisation are soluble

113
Q

Why can phenol act as an acid with string bases

A

Forms the phenoxide ion C6H5O-

C6H5OH becomes C6H5O- and H+

114
Q

Reaction of phenol with NaOH

A

NaOH and C6H5OH becomes C6H5O-Na+ and H2O

115
Q

Why does phenol not react with CO32-

A

Phenol is not a strong enough acid

116
Q

What is a primary amine

A

R-N-H2

An amine with one alkyl chain attached to an N in amine

117
Q

What is a secondary amine

A

R-N-HR’

An amine with 2 alkyl groups attached to the N

118
Q

What is a tertiary amine

A

R-N-R’R”

Am amine with 3 alkyl chains attached to the N

119
Q

What does N notation represent (eg N-methylpropane)

A

That the alkyl chain is attached directly to the N atom

120
Q

Bonding in primary, secondary and tertiary amines

A

Primary and secondary amines have London forces, permanent dipole interactions and H bonding

Tertiary amines have London forces and permanent dipole

121
Q

Solubility of amines

A

Small amines are soluble

Solubility decreases as the size of the alkyl chain increases

122
Q

What is the Brønsted-Lowry definition of a base

A

A base is a proton (H+ hydrogen ion) acceptor

123
Q

What is the Lewis definition of a base

A

A base is an electron pair donor

124
Q

What does a Kb value tell us

A

Large Kb value means [products] is greater than [reactants]

The larger the Kb the further right the position of equilibrium

The larger the Kb value, the stronger the base

125
Q

Why are longer alkyl chain amines more basic

A

Greater inductive effect causes more electron density to be pushed into N atom

Means N atom more readily attracts a H+

126
Q

Why is phenylamine not as basic as would be expected

A

The lone pair of electrons on the N overlap with the delocalised electrons on the benzene ring

Causes reduction in electron density

Means it is difficult to attract a H+

127
Q

Reagents and conditions to synthesise and aliphatic amine

A

Reagents- Halogenoalkane, ammonia

Conditions- high temp, sealed tube

128
Q

What are aliphatic amines synthesised from

A

Halogenoalkanes

129
Q

What type of reaction occurs in the production of an aliphatic amine

A

Nucleophilic substitution

130
Q

How is further substitution prevented to synthesise a primary amine

A

Excess ammonia is used- ensures all the Halogenoalkane is used up

131
Q

What is produced if the Halogenoalkane is not entirely used up in the synthesis of a primary aliphatic amine

A

A secondary aliphatic amine is produced

132
Q

If I reacted Halogenoalkane is present after the production of a secondary amine, what will happen

A

The reaction will continue to occur

133
Q

Conditions and reagents for forming an amine from a nitrile

A

Reagent: LiAlH4

Conditions : dry ether

134
Q

Standard equation for forming amine from nitrile

A

R-CN + 4[H] becomes R-C-NH2

135
Q

Why do aromatic amines not react with ammonia

A

The high electron density of the benzene ring repels ammonia

136
Q

Equation for reaction of a primary amine acting as a base

A

RNH2 + H+ becomes RNH3+

137
Q

Equation for secondary amine acting as a base

A

RR’NH + H+ becomes RR’NH2+

138
Q

Equation for tertiary amine acting as a base

A

RR’R”N + H+ becomes RR’R”NH+

139
Q

How does an amine act as a base in a complex ion

A

It accepts a proton from the water ligands

140
Q

Functional group of an amide

A

O=C-NH

141
Q

What is a quaternary ammonium salt and is it an amine

A

A N with 4 alkyl groups attached

It is not an amine

142
Q

What variable affects the base strength of an amine

A

The electron density on the N atom

143
Q

Why can nucleophilic substitution continue to occur with amines

A

Amines produced all have a lone pair on the N atom, so they can continue to react

144
Q

In a reaction between a Halogenoalkane and ammonia, what is the main product if ammonia is in a large excess

A

Primary amine

145
Q

In a reaction between a Halogenoalkane and ammonia, what is the main product if Halogenoalkane is in a large excess

A

Quaternary ammonium salt

146
Q

What are the uses of properties ammonium salts

A

Contain an ionic “head”- dissolve in water and are hydrophilic

A long alkyl chain “tail”- dissolves grease and is hydrophobic

147
Q

Equation to form primary aromatic amine

A

C6H5NO2 + 4[H] becomes C6H5NH2 + 2H2O

148
Q

Conditions and reagents to form primary aromatic amine

A

Tin, conc HCl then later NaOH

149
Q

Steps to form an amine from a nitrile

A

Formation of nitrile from Halogenoalkane: R-X and KCN becomes R-CN and KX

Reduction of nitrile to an amine
R-CN + 4[H] becomes R-CH2-NH2

150
Q

What is acylation of an amine

A

Where an amine and an acyl chloride react to replace an H on the N with an alkyl group

Produces an amine and a molecule of HCl/ carboxylic acid

Second molecule of amine reacts with HCl/carboxylic acid to form a salt

151
Q

Standard equation for acylation of amine

A

R-CO-Cl + 2 R’-NH2 becomes R-CO- NHR’ and N+-H3R’

152
Q

What two functional groups are contained in an amino acid

A

Amine
Carboxylic acid

153
Q

Why do amino acids acts as both acids and bases

A

Amine functional group is basic

Carboxylic acid functional group is acidic

154
Q

What are zwitterions

A

Ions formed by the internal transfer of a proton

155
Q

Properties of amino acids and explanations

A

High melting point- strong electrostatic forces require lots of energy to overcome

Soluble- form ion/dipole interactions with water molecules, which release enough energy to overcome IMFs between water molecules and electrostatic forces between zwitterions

156
Q

Attraction of zwitterions and property this gives

A

Strong electrostatic attraction between other zwitterions

Allows them to exist in the solid state

157
Q

Equation for amino acid acting as a base

A

H2N-CHR- COOH becomes H2N-CHR—COO + H2O

158
Q

Equation for amino acid acting as an acid

A

H2N-CHR-COOH becomes H3N-CHR-COOH

159
Q

Affect on amino acid if reacted with NaOH

A

Amino acid loses a H

160
Q

Affect if amino acid reacts with HCl

A

Gains a H

161
Q

Affect when amino acid reacts with ethanol in presence of small amount of conc H2SO4

A

Ester group formed

162
Q

Affect when amino acid reacts with ethanol chloride

A

Amide bond formed

163
Q

How are peptides formed

A

In a condensation reaction between amino acids

164
Q

What is a peptide bond

A

An amide bond

-HN-CO-

165
Q

What is polypeptide

A

The result of 50+ amino acids joining in a chain

166
Q

How does the condensation reaction between amino acids occur

A

The amine group on one amino acid attacks the C atom of the carboxylic acid group of another amino acid

A molecule of water is lost

167
Q

What is the result of a condensation reaction between amino acids

A

A secondary amide group that links the two amino acid residues together

168
Q

How to identify amino acids

A

Break down the polypeptide using hydrolysis

Separate and identify amino acids produced using TLC:
Amino acids are colourless- need to be sprayed with a locating agent and heated
Locating agent forms coloured compound

Calculate the retention factor of amino acid

Compare Rf value to known value

169
Q

What is the hydrolysis of polypeptides

A

The breaking down of the polypeptide into the amino acid monomers

170
Q

Conditions and reagents for hydrolysis of polypeptides

A

Reflux with conc HCl

171
Q

What is addition polymerisation

A

Where lots of monomers join together to form a longer molecule

Occurs with unsaturated monomers eg C=C

100% atom economy

172
Q

Equation to produce poly(ethene) from ethene

A

H2C=CH2 becomes -H2C-CH2-

173
Q

What is condensation polymerisation

A

The removal of a small molecule, eg H2O or HCl, to form a polymer

174
Q

What is used to form a polyester

A

A dialcohol and a dicarboxylic acid

175
Q

What is a diol

A

A dialcohol eg HO-CH2-CH2-OH

176
Q

Standard equation for forming a polyester

A

HO-CH2-R-CH2-OH + HOOC-R-COOH becomes -O-CH2-R-CH2-O-CO-CO- +2H2O

177
Q

What atoms are lost to form a polyester

A

The H atoms from the diol -OH group s and the OH from the -COOH carboxylic acid group

178
Q

Why is a polyamide also known as

A

A nylon

179
Q

How are polyamides formed

A

Diamine and dicarboxylic acid

Diamine and diacylchloride

Amino acid

180
Q

Standard equation for formation of polyamide

A

H2N-R-NH2 + HOOC-R-COOH becomes -HN-R-NH-OC-R-CO- + 2H2O

181
Q

What atoms are lost in the formation of a polyamide

A

A H from each -NH2 amine group

OH from each -COOH carboxylic acid group

182
Q

What is an AAA polymer

A

Where only one monomer is used to form the polymer

183
Q

What is an ABAB polymer

A

Where copolymerisation occurs- more than one monomer used

184
Q

What can a condensation polymer be AAA

A

If the monomer is bifunctional- it contains a carboxylic acid/acyl chloride group and a amine/hydroxyl group

185
Q

Properties of any nylons

A

Tough and Durable

High tensile strength due to H bonding between polymer chains

186
Q

How are polyamides named

A

Nylon- x,y

Where x is the number of C atoms in the Diamine and y is the number of C atoms in the dicarboxylic acid

187
Q

How can you extend the length of a Carbon chain

A

Halogenoalkane and CN-

Carbonyl and CN-

Friedel-crafts alkylation

Gringards reagents

188
Q

What is a gringards reagent and give its formula

A

A gringards reagent is an organometallic compound used to extend a carbon chain

R-Mg-X where R is an alkyl chain and X a halogen

189
Q

Why do gringards reagents typically not use F or Cl as it’s halogen

A

The C-F and C-Cl bonds are very strong, making it difficult to synthesise the reagent

190
Q

Conditions and reagents for synthesis of gringards reagent

A

Reagents- Halogenoalkane and Mg turnings

Conditions- dry ether, I2 catalyst and reflux

191
Q

Standard equation for synthesis of gringards reagent

A

RMgX + H2O becomes RH + Mg(OH)X

192
Q

Why is the whole reaction mixture used as a gringards reagent

A

Gringards reagents are difficult to isolate

Using whole reaction mixture is easier

193
Q

Why are gringards reagents very reactive

A

A S- C atom is very unstable, so the S- C in the Gringards Reagant will attach a S+ C in another reagent

194
Q

Reaction of Gringards reagents with Carbon Dioxide and how much longer is the C chain made

A

CO2 + RMgBr becomes RCOOH

C chain made one C longer

195
Q

Reaction of Gringards reagents with methanal and how much longer is the C chain made

A

CH2O + RMgBr becomes RCH2OH

Forms primary alcohol- C chain extended by one C atom

196
Q

Reaction of Gringards reagents with an aldehyde (not methanal) and how much longer is the C chain made

A

CHRO + RMgBr becomes CRR’HOH

Forms secondary alcohol- extension of chain determined by the R group on the aldehyde

197
Q

Reaction of Gringards reagents with ketone and how much longer is the C chain made

A

CRR’O + RMgBr becomes CRR’R”OH

Forms a tertiary alcohol

C chain extension dependant on alkyl groups

Chemsitry (15 decks)

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