IB Chemistry Topic 10/20

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What is the structure of benzene

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1

What is the structure of benzene

Each carbon atom is sp hybridised and forms 3 sigma bonds

The unhybridised p orbitals overlap in both directions, forming a delocalised pi electron cloud.

This means the electron density is concentrated in donut shaped rings above and below the plane of the ring.

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2

How are esters named

The alcohol group name is at the start, followed by the carboxylic acid group name.

eg. methanoic acid + ethanol → ethyl methanoate

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3

What is the Sn2 mechanism and how does it occur

Sn2 occurs in primary halogenoalkanes, where at least 2 H atoms are attached to the C of the C-H bond

The carbon is open to attack by the nucleophile due to the small size of the H atoms

An unstable transition state is formed where the C is weakly bonded to both the halogen and the nucleophile

The C-halogen bond breaks heterolytically and the halogen is released.

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4

How does the arrangement of the atoms change in the Sn2 mechanism

The nucleophile attacks the C on the opposite side from the leaving group, causing an inversion in the arrangement.

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5

When does Cis-trans and E-Z isomerism occur

In a double bond, as there is no free rotation

And in cycloalkanes

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6

What are cis-trans isomers

Where the molecule contains 2+ different groups attached to the double bond/ring

Cis isomers are where the groups are on the same side of the double bond/ring

Trans isomers have the group on opposite sides.

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7

When is E-Z isomerism used

When all the groups are different attached to the double bond, so no same groups can be distinguished.

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8

How do the rules of priority determine the E-Z structure

  1. If the groups are singular atoms, the highest atomic number has priority

  2. Longer hydrocarbon chains have higher priority

If the 2 highest priority groups are on the same side it is a Z isomer

If the 2 highest priority groups are on opposite sides it is a E isomer

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9

What are stereoisomers

A chiral carbon (C attached to 4 different groups) is the stereocentre of a stereoisomer.

They have 2 different enantiomers which are mirror images of each other

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10

What is a racemic mixture

Where a mixture contains equal amounts of 2 enantiomers.

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11

How can we distinguish between 2 enantiomers

They rotate in plane polarised light in opposite directions.

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12

What kind of reaction do alkanes take part in

free radical substitution (halogenation)

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13

What is the initial stage of halogenation

Initiation stage

The halogen is broken from a diatomic molecule to 2 monatomic atoms by UV light

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14

What occurs in the propagation stage of halogenation

The halogen free radical react with the alkane, making alkyl free radicals and hydrogen (halogen)

The second free radical can react with another alkane

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15

What occurs in the termination stage of halogenation

2 free radicals collide to end the chain reaction.

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16

Which reactants perform electrophilic addition

Alkene + halogen

Alkene + hydrogen halide

Alkene + steam (with catalyst)

Alkene + hydrogen (with nickel catalyst and 150 degrees)

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17

What is the first step of electrophilic addition

The electrophile attacks the pair of electrons in the double bond . This forms a positive carbocation intermediate and breaks the bond in the electrophile heterolytically.

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18

What is the second step of electrophilic addition

The negative ion remaining from the heterolytic fission of the electrophile the attacks the carbon atom holding the positive charge on the intermediate.

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19

what conditions are needed to dehydrate a alcohol

Heating at 170 degrees

With concentrated phosphoric acid, sulfuric acid or hot aluminium oxide

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20

What are primary alcohols oxidised to

aldehydes

And they can be further oxidised into carboxylic acids

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21

What are secondary alcohols oxidised to

ketones, occurs under reflux

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22

What are tertiary alcohols oxidised to

they do not oxidise

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23

Why do halogenoalkanes undergo substitution

Because there is a dipole as the C-Halogen bond has an electronegativity difference.

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24

What does the strength of a carboxylic acid depend on

The ease with which the O-H bond is broken

This is affected by groups on the carbon chain which reduce the strength of the O-H bond, this makes it more acidic

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25

How are carboxylic acids reduced

They are reduced to aldehydes, by using strong reducing agents such as lithium aluminium hydride.

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