Module 6 ( Organic )

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40 Terms

1
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what is the molecular formula benzene

C₆H₆

2
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what is the bond angle and shape of carbons in benzene

120°C

trigonal planar

3
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what type of molecule is benzene ?

Cyclic

4
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what is the general formula of benzene

CₙHₙ

5
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what forms the delocalised π ring in benzene

the fourth e⁻ is delocalised

the lone e⁻ in the p-orbital overlap to form a delocalised ring of electrons

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what are the two structures/ models of benzene

Kekule model

the delocalised model

7
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which experimental data proves that kekule model is incorrect

C-C bonds are the same length / in kekules bonds would have different lengths and strengths because of the C=c bonds

Benzene is unreactive and doesn't undergo addition reactions readily

∆H Hydrogenation is about 152 kjmol⁻1 less then expected

8
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why is benzene unreactive?

due to the delocalised ring of π 6 electrons in 6 p-orbitals

hard to break the π ring

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another name for kekule structure

triene

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how do we know benzene doesn't contain C=C

Bromine water doesn't react with benzene

no visible change

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what is the bonding in benzene

Carbons have 3 covalent bonds

spare lone electron in the p-orbital overlap to form delocalised π ring

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What are arenes/aromatic compounds?

molecules containing a benzene ring

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how to name benzene

when benzene is the main functional group ( C₆H₆) --> the suffix is benzene

when benzene isn't main functional group, the molecule is named as a phenyl group - prefix

the suffix comes from other molecule

14
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naming benzene ( image)

Give functional group lowest number

<p>Give functional group lowest number</p>
15
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what is a phenyl group molecule formula

C₆H₅

16
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similarities between kekule and delocalised structure of benzene

both have p-orbitals overlapping sideways

π bond above and below plane of carbon atoms

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Phenol image

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molecular formula of Phenol

C₆H₅OH

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what the 2 reactions benzene undergoes

Nitration

Halogenation

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what is the only type of reaction benzene undergoes

Electrophilic substitution

21
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what is the overall equation for the nitration of Benzene

C₆H₆ + HNO₃ → C₆H₅NO₂ + H₂O

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catalyst in the nitration of benzene

Concentrated H₂SO₄

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why is the catalyst in nitration of benzene the catalyst

H₂SO₄ is reformed during the reaction

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effects of using higher temperatures in the nitration of benzene

Forms Poly nitro benzenes instead of mono

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how to form nitro benzene

React benzene with Nitric acid ( HNO₃)

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what are the 3 steps in electrophilic substitution reactions

Step 1 —> forming the electrophile

Step 2 —> electrophile attack ( Mechanism)

Step 3 —> reforming the catalysts

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equation for forming the nitronium ion

HNO₃ + H₂SO → NO₂⁺ + HSO₄⁻ + H₂O

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Electrophilic substitution ( Nitration) mechanism

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Equation to reform the catalyst in the nitration of benzene

HSO₄ + H⁺ → H₂SO₄

H⁺ comes from the mechanism

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what is the nitration of benzene

benzene + Nitric acid

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general equation for the Halogenation of benzene

C₆H₆ + X₂ → C₆H₅X + HX

X= Cl / Br

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what are the catalysts for the halogenation of benzene

Halogen carriers

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what are the halogen carriers

aluminum chloride (AlCl₃)

Iron bromide (FeBr₃)

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what is the electrophile in the Nitration of benzene

NO₂⁺

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what is the electrophile in the halogenation of benzene

Cl⁺/Br⁺

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equations for making the electrophile in the halogenation of Benzene

AlCl₃ + Cl₂ → AlCl₄⁻ + Cl⁺

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how is the electrophile formed in the halogenation of benzene

Halogen carrier reacts with the halogen forming a halogen carrier ( 4 halogens ) anion and a halogen cation

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Electrophilic substitution ( Halogenation) mechanism

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Equations to reform catalyst halogenation of benzene

AlCl₄⁻ + H⁺ → AlCl₃ + HCL

40
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Why do we use halogen carriers for Benzene and not alkenes

Benzene has a delocalised π bond ring makes it too stable

Alkenes has a localised π bond which is less stable