Making Aldehydes and Ketones from Alkenes and Alkynes (Ozonolysis and Alkyne Hydration)

Chemistry · Aldehydes, Ketones And Carboxylic Acid · NEET

There are two ways to make carbonyl compounds from hydrocarbons. First, ozonolysis of an alkene: treat it with ozone (O3), then with zinc dust and water (Zn/H2O). This cuts the C=C double bond into two pieces, and each piece gets a C=O. Second, hydration of an alkyne: add water using H2SO4 and HgSO4. Only ethyne gives an aldehyde (acetaldehyde); every other alkyne gives a ketone. Memory hook: "Cut the double bond, both ends become C=O. Only ethyne is special and gives an aldehyde."
Two routes: hydrocarbon to carbonyl (C=O)1. Ozonolysis of alkene (CUT the C=C)R-CH=CH-R'(1) O3(2) Zn / H2OR-CHO + R'-CHOeach end gets =O; H-bearing end = aldehyde2. Hydration of alkyne (ADD water)HC≡CH (ethyne)H2O, H2SO4HgSO4CH3-CHO (acetaldehyde)only ethyne = aldehyde; other alkynes = ketone
Two hydrocarbon routes to carbonyls: ozonolysis cuts an alkene's C=C into two aldehydes/ketones (Zn/H2O keeps them from over-oxidising), while alkyne hydration adds water; only ethyne gives an aldehyde and all other alkynes give ketones.

Your doubts, answered

What exactly is the product when I do ozonolysis of an alkene?

The C=C double bond breaks in the middle. Each carbon that was part of the double bond now becomes a carbonyl carbon (C=O). So one alkene gives two carbonyl compounds (or one if the molecule is symmetric). Rule: look at each doubly-bonded carbon. If it has an H attached, that end becomes an ALDEHYDE. If it has two carbons attached (no H), that end becomes a KETONE. Example: CH3-CH=CH-CH3 gives two molecules of CH3CHO (ethanal).

Why do we add Zn dust and water after ozone? Can I skip it?

No. Ozone first makes an unstable ozonide. Zinc dust and water (reductive workup) break that ozonide gently to give aldehydes and ketones. If you skip Zn and use water alone (oxidative workup), the aldehydes get over-oxidised to carboxylic acids. For NEET, the standard reagent set is O3 followed by Zn/H2O and the products are aldehydes/ketones, NOT acids. This is a very common trap.

Which alkyne gives an aldehyde and which gives a ketone on hydration?

Only ethyne (HC≡CH, the smallest alkyne) gives an aldehyde, which is acetaldehyde (CH3CHO). Every OTHER alkyne gives a ketone. The reagents are water with H2SO4 and HgSO4 (mercuric sulphate as catalyst). Reason: water adds by Markovnikov rule to form an unstable enol, which rearranges (tautomerises) to the carbonyl. For ethyne both carbons are equal, so you get an aldehyde; for higher alkynes the OH lands on the more substituted carbon, giving a ketone.

What is the difference between ozonolysis and alkyne hydration?

Ozonolysis starts from an alkene (C=C) and BREAKS the molecule into two carbonyl pieces. Alkyne hydration starts from an alkyne (C≡C) and does NOT break the molecule; it just ADDS water across the triple bond to give ONE carbonyl compound with the same number of carbons. So ozonolysis = cut and count two products; hydration = add water and keep one product.

How do I quickly predict ozonolysis products in the exam?

Step 1: Draw the alkene and find the C=C. Step 2: Cut it in half; put =O on each carbon that was in the double bond. Step 3: For each new carbonyl carbon, if it still has an H, it is an aldehyde; if it has two carbon groups, it is a ketone. Symmetric alkenes give one product (double amount); unsymmetrical alkenes give two different products.

⚠️ The NEET trap
Ozonolysis of an alkene with O3 followed by Zn/H2O gives carboxylic acids.
With the REDUCTIVE workup Zn/H2O, ozonolysis stops at aldehydes and ketones, not carboxylic acids. Carboxylic acids would form only under an oxidative workup (e.g. H2O2/water without Zn). NEET expects aldehydes/ketones for the O3, Zn-H2O set.
🧠 See Zn in the workup? Then STOP at C=O. No Zn = danger of over-oxidation to COOH.

Real NEET questions

NEET 2024

Match List-I with List-II and choose the correct option. List-I (Reaction): (a) C6H6 -> C6H5-CO-C6H5 (benzophenone); (b) Alkene -> carbonyl (oxidative cleavage); (c) C6H5-OH -> carbonyl (oxidation); (d) C6H5-CH2-CH3 -> C6H5-COOH. List-II (Reagents/Condition): (i) C6H5COCl, anhyd. AlCl3; (ii) CrO3; (iii) KMnO4/KOH, heat; (iv) (1) O3, (2) Zn-H2O.

A · (a)-(iii), (b)-(i), (c)-(ii), (d)-(iv)
B · (a)-(iv), (b)-(i), (c)-(ii), (d)-(iii)
C · (a)-(i), (b)-(iv), (c)-(ii), (d)-(iii)
D · (a)-(iv), (b)-(i), (c)-(iii), (d)-(ii)
Solution: The clue for this concept is (b): an alkene is cleaved to carbonyl compounds by ozonolysis, so (b) pairs with (iv) O3 then Zn-H2O. Also: (a) benzene to benzophenone is Friedel-Crafts acylation with C6H5COCl/AlCl3 = (i); (c) phenol oxidised by CrO3 = (ii); (d) ethylbenzene side-chain oxidised by KMnO4/KOH, heat to benzoic acid = (iii). This gives (a)-(iv), (b)-(i), (c)-(ii), (d)-(iii), which is option (B).

Solved Aldehydes, Ketones And Carboxylic Acid NEET PYQs

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Frequently asked

Does ethene give formaldehyde on ozonolysis?

Yes. Ethene (CH2=CH2) is symmetric, so cutting the C=C gives two molecules of methanal (formaldehyde, HCHO).

What catalyst is used in alkyne hydration?

Water is added in the presence of dilute H2SO4 with HgSO4 (mercuric sulphate) acting as the catalyst. Ethyne then gives acetaldehyde; higher alkynes give ketones.

Why does the enol turn into a carbonyl in alkyne hydration?

The first product is an enol (C=C with an OH). Enols are unstable and rearrange by keto-enol tautomerism to the more stable keto form, which is the aldehyde or ketone.

Is ozonolysis an addition or a cleavage reaction?

It is an oxidative cleavage. Ozone adds across the double bond first, but the final result breaks the molecule into two carbonyl fragments, so it counts as cleavage for NEET.

Can a symmetric alkyne give an aldehyde?

No. Only terminal ethyne gives an aldehyde. Symmetric internal alkynes like but-2-yne give a single ketone; the products are always ketones for any alkyne except ethyne.