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OCR A Level Chemistry A – Module 6 Organic Chemistry and Analysis

6.2.4
Carbon–Carbon
Bond Formation

Section 6.2.4 covers the use of C–C bond formation in synthesis to lengthen a carbon chain (a): forming nitriles from haloalkanes with cyanide and from carbonyl compounds with HCN, with both mechanisms (b), reducing the nitrile to an amine or hydrolysing it to a carboxylic acid (c), and forming a substituted aromatic C–C bond by Friedel–Crafts alkylation and acylation with a halogen carrier (d). The route-planning page shows where each C–C step fits in a multi-stage synthesis.

Exam Paper
Paper 2 & 3
H432/02 and H432/03
Learning Outcomes
6.2.4 (a) – (d)
4 learning outcomes
Sub-topics
2 lessons
Revision notes available
Exam Board
OCR
H432 (2015 onwards)

Revision Notes

2 revision notes, in the order the specification teaches them.

Two carbon chains joined by a glowing new bond
1

Carbon–Carbon Bond Formation

Forming carbon–carbon bonds in synthesis: the nitrile routes from haloalkanes and carbonyl compounds and Friedel–Crafts reactions.

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A multi-step synthesis route
2

Planning a Synthetic Route

Planning multi-step organic synthesis routes: the reaction map, working backwards from the target.

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Summary Map

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Summary maps

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Illustration of a summary map: compounds joined by reaction arrows
Summary map · PDF

Nitriles Map

OCR A Level Chemistry A · 6.2.4 Carbon–carbon bond formation

Every reaction on one A4 page: reagents, conditions and reaction type for each arrow, colour coded, with the key tests.

Download the map2 reactions · A4 landscape · print ready
Illustration of a summary map: compounds joined by reaction arrows
Summary map · PDF

Carbon-Carbon Bonds Map

OCR A Level Chemistry A · 6.2.4 Carbon-carbon bond formation

All of 6.2.4 on one A4 page: making and using nitriles, both mechanisms, and Friedel–Crafts reactions.

Download the map6 key ideas + worked examples · A4 portrait · print ready

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Revision Game

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Revision Game: Carbon–carbon bond formation

Turn the cards over two at a time: match reagents to what they make, and find how each product is made.

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Specification

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6.2.4

  1. a

    the use of C–C bond formation in synthesis to increase the length of a carbon chain (see also 6.1.1 d, 6.1.2 b)

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  2. b (i) a

    formation of C–C≡N by reaction of haloalkanes with CN– and ethanol (see also 4.2.2 c)

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  3. b (i) b

    the nucleophilic substitution mechanism for the reaction of haloalkanes with CN– and ethanol (see also 4.2.2 c)

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  4. b (ii) a

    formation of C–C≡N by reaction of carbonyl compounds with HCN (see also 6.1.2 b–c)

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  5. b (ii) b

    the nucleophilic addition mechanism for the reaction of carbonyl compounds with HCN (see also 6.1.2 b–c)

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  6. c (i)

    reaction of nitriles from (b) by reduction (e.g. with H2/Ni) to form amines

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  7. c (ii)

    reaction of nitriles from (b) by acid hydrolysis to form carboxylic acids

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  8. d i

    formation of a substituted aromatic C–C by alkylation (using a haloalkane) in the presence of a halogen carrier (Friedel–Crafts reaction) (see also 6.1.1 d)

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  9. d ii

    formation of a substituted aromatic C–C by acylation (using an acyl chloride) in the presence of a halogen carrier (Friedel–Crafts reaction) (see also 6.1.1 d)

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