Pyridinium chlorochromate· PCC
Transformation
Exam tip / mistake to avoid
Mistake to avoid: PCC normally stops a primary alcohol at the aldehyde. Do not confuse it with strong aqueous dichromate, which can continue oxidation to the acid.
Use the interactive explorer below to revise common organic chemistry reagents by transformation, reaction conditions, and exam-focused clues.
First identify the functional group in the starting material. Then ask what the reagent is designed to change: oxidation level, reduction level, leaving group, carbon skeleton, or a diagnostic test. Conditions matter because the same reagent family can give different products under controlled or vigorous conditions.
This is a revision guide for common laboratory and examination reactions. Always follow an approved laboratory protocol and the relevant safety data sheet when handling chemicals.
Chemistry Reagent Explorer is a fundamental concept in organic chemistry. Understanding the mechanisms, reaction conditions, and stereo-chemical outcomes is crucial for mastering organic chemistry. Our curated resources provide step-by-step visualizations to help you excel.
Transformation
Exam tip / mistake to avoid
Mistake to avoid: PCC normally stops a primary alcohol at the aldehyde. Do not confuse it with strong aqueous dichromate, which can continue oxidation to the acid.
Transformation
Exam tip / mistake to avoid
The purple colour disappears with oxidisable unsaturation. Do not assume every KMnO₄ condition gives the same product.
Transformation
Exam tip / mistake to avoid
Orange dichromate turns green. For a primary alcohol, remember that reflux favours complete oxidation to the carboxylic acid.
Transformation
Exam tip / mistake to avoid
Mistake to avoid: LiAlH₄ is moisture-sensitive. Add water or acid only during the work-up, never during the hydride step.
Transformation
Exam tip / mistake to avoid
NaBH₄ is milder than LiAlH₄. In standard conditions it usually reduces aldehydes and ketones without reducing esters or carboxylic acids.
Transformation
Exam tip / mistake to avoid
Hydrogenation adds H₂ across a π bond. Do not forget that catalyst, pressure, and selectivity affect the product.
Transformation
Exam tip / mistake to avoid
Mistake to avoid: Tollens’ reagent is a test for aldehydes, not a general test for every carbonyl compound. Most ketones give no silver mirror.
Transformation
bromine colour is discharged
Exam tip / mistake to avoid
The orange-brown colour disappears with an alkene. Do not call this an oxidation test: it is electrophilic addition across C=C.
Transformation
Exam tip / mistake to avoid
SOCl₂ replaces –OH with Cl. Remember that SO₂ and HCl are by-products, so the reaction is often driven forward as gases escape.
Transformation
Exam tip / mistake to avoid
For a chiral alcohol reacting through an SN2 pathway, expect inversion of configuration.
Transformation
Exam tip / mistake to avoid
Mistake to avoid: water destroys the Grignard reagent. Keep the carbon–magnesium step dry and add acid only during work-up.
Transformation
Exam tip / mistake to avoid
Alcoholic KOH favours elimination, while aqueous KOH more commonly favours substitution.
SELF TEST
Which reagent most commonly oxidises a primary alcohol to an aldehyde without normally continuing to the acid?
LEARNING SUPPORT
Conditions can change the strength and selectivity of a reagent. For example, PCC commonly stops a primary alcohol at an aldehyde, while strong aqueous dichromate can oxidise it further to a carboxylic acid.
Sodium borohydride (NaBH4) is a mild hydride reducing agent commonly used to convert aldehydes and ketones into primary and secondary alcohols, respectively.
A Grignard reagent behaves as a strong base as well as a nucleophile. Water, alcohols, and other acidic hydrogen sources protonate it and destroy the carbon nucleophile.