Organic Mechanisms (AQA A Level Chemistry): Revision Note

Exam code: 7405

Stewart Hird

Written by: Stewart Hird

Reviewed by: Caroline Carroll

Updated on

Organic Mechanisms

Organic Mechanisms

  • Throughout the A-Level course, students have met several organic mechanisms

  • The reaction mechanisms covered in this course are:

    • Free radical substitution

    • Electrophilic addition

    • Nucleophilic substitution

    • Elimination

    • Nucleophilic addition

    • Nucleophilic addition-elimination

    • Electrophilic substitution

    • Formation of amides

Examiner Tips and Tricks

You must be able to provide these mechanisms in full if asked for. You must be able to apply your knowledge of what happens in a reaction mechanism to other reactions.

General Mechanisms

  • The general mechanisms for each of these reactions are shown below

  • Remember, these are just general mechanisms - for the exam, students will have to draw them specific to the reaction in the exam question

Free radical substitution

Diagram showing the three stages of free radical substitution: initiation with UV light breaking a Cl-Cl bond homolytically, propagation chain reactions, and termination by radical combination
Free radical substitution proceeds through initiation, propagation and termination steps — curly arrows are not used for this mechanism

Related links

Examiner Tips and Tricks

In free-radical mechanisms, half-headed arrows are not required, but using double-headed arrows will be penalised. Radical dots must be shown in free-radical substitution — absence is penalised.

Electrophilic addition

Diagram showing electrophilic addition mechanism with a curly arrow from the C=C double bond to the electrophile, forming a carbocation intermediate, followed by nucleophilic attack
In electrophilic addition, the electron-rich pi bond attacks the electrophile to form a carbocation intermediate

Related Links

Examiner Tips and Tricks

When drawing carbocation intermediates, do not draw a bond to the positive charge — the charge must sit on the carbon atom.

Nucleophilic substitution

Diagram showing nucleophilic substitution with a curly arrow from the nucleophile lone pair attacking the delta-positive carbon of a halogenoalkane as the halide departs.
Nucleophilic substitution involves attack by a nucleophile on a delta-positive carbon as the halide ion leaves

Related links

Examiner Tips and Tricks

Partial charges must be placed on the correct atoms (e.g., δ+ on C and δ- on X in C-X).

Nucleophilic substitution with ammonia

Diagram showing nucleophilic substitution with ammonia attacking the delta-positive carbon, followed by deprotonation.
With ammonia as the nucleophile, a further deprotonation step removes a hydrogen to form the amine product

Elimination

Diagram showing elimination mechanism with a base removing a hydrogen adjacent to the C-X bond, forming a C=C double bond as the halide leaves.
Elimination produces an alkene by removal of a hydrogen atom and a halide from adjacent carbons

Related links

Examiner Tips and Tricks

If a C-H bond is broken in a mechanism (e.g., elimination), both the bond and the H atom must be drawn explicitly — "sticks" lose marks here.

Nucleophilic addition

Diagram showing nucleophilic addition to a carbonyl group with a curly arrow from the nucleophile lone pair to the delta-positive carbon.
In nucleophilic addition, the nucleophile attacks the planar delta-positive carbon of the carbonyl group

Related links

Nucleophilic addition-elimination

Diagram showing nucleophilic addition-elimination with attack on an acyl chloride, tetrahedral intermediate formation, and departure of the chloride leaving group.
Nucleophilic addition-elimination involves initial addition to the carbonyl carbon followed by loss of the leaving group

Related links

Electrophilic substitution

Diagram showing electrophilic substitution on a benzene ring with formation of a sigma complex intermediate, restoration of aromaticity and loss of H+
Electrophilic substitution preserves the aromatic ring by restoring the delocalised system after substitution

Related links

Formation of Amides

Diagram showing amide bond formation between an amine and an acyl chloride via nucleophilic addition-elimination mechanism
Amide formation is an example of nucleophilic addition-elimination between an amine and an acyl chloride

Examiner Tips and Tricks

Curly arrows must originate from a lone pair or from a bond — arrows starting at an atom score zero.

When showing bond formation, the arrow must go directly to the relevant atom, not to a formal charge.

Drawing extraneous curly arrows (e.g., from a breaking C-Br bond to a spectator K⁺ ion) loses marks.

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Stewart Hird

Author: Stewart Hird

Expertise: Chemistry Content Creator

Stewart has been an enthusiastic GCSE, IGCSE, A Level and IB teacher for more than 30 years in the UK as well as overseas, and has also been an examiner for IB and A Level. As a long-standing Head of Science, Stewart brings a wealth of experience to creating Topic Questions and revision materials for Save My Exams. Stewart specialises in Chemistry, but has also taught Physics and Environmental Systems and Societies.

Caroline Carroll

Reviewer: Caroline Carroll

Expertise: Head of Content Delivery

Caroline graduated from the University of Nottingham with a degree in Chemistry and Molecular Physics. She spent several years working as an Industrial Chemist in the automotive industry before retraining to teach. Caroline has over 12 years of experience teaching GCSE and A-level chemistry and physics. She is passionate about delivering high-quality resources to help students achieve their full potential.