chemistry

Thiol-yne reaction

Thiol-yne reaction is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Thiol-yne reaction rather than just read about it. In short: In organic chemistry, the thiol-yne reaction (also known as alkyne hydrothiolation) is an organic reaction between a thiol (−SH) and an alkyne (−C≡CH). The reaction product is an alkenyl sulfide (−CH=CH−S−).

Key takeaways

Thiol-yne reaction belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Thiol-yne reaction to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Thiol-yne reaction from memory before moving on to harder problems.

Reference excerpt

In organic chemistry, the thiol-yne reaction (also known as alkyne hydrothiolation) is an organic reaction between a thiol (−SH) and an alkyne (−C≡CH). The reaction product is an alkenyl sulfide (−CH=CH−S−). The reaction was first reported in 1949 with thioacetic acid as reagent and rediscovered in 2009. It is used in click chemistry and in polymerization, especially with dendrimers.

This addition reaction is typically facilitated by a radical initiator or UV irradiation and proceeds through a sulfanyl radical species. With monoaddition a mixture of (E/Z)-alkenes form. The mode of addition is anti-Markovnikov. The radical intermediate can engage in secondary reactions such as cyclisation. With diaddition the 1,2-disulfide or the 1,1- dithioacetal forms. Reported catalysts for radical additions are triethylborane, indium(III) bromide and AIBN. The reaction is also reported to be catalysed by cationic rhodium and iridium complexes, by thorium and uranium complexes, by rhodium complexes, by caesium carbonate and by gold.

Diphenyl disulfide reacts with alkynes to a 1,2-bis(phenylthio)ethylene. Reported alkynes are ynamides. A photoredox thiol-yne reaction has been reported.

Polymer chemistry In polymer chemistry, systems have been described based on addition polymerization with 1,4-benzenedithiol and 1,4-diethynylbenzene, in the synthesis of other addition polymer systems in the synthesis of dendrimers, in star polymers, in graft polymerization, block copolymers, and in polymer networks. Another reported application is the synthesis of macrocycles via dithiol coupling.

See also Click chemistry Michael addition Radical addition Thiol-ene reaction

References

Illustrations

Worked examples

Example 1 — a first encounter with Thiol-yne reaction

Start with the simplest possible case. Write down what Thiol-yne reaction claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Thiol-yne reaction before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Thiol-yne reaction ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Thiol-yne reaction

In research: Thiol-yne reaction appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Thiol-yne reaction in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Thiol-yne reaction is common in secondary-school and first-year university syllabi. It links to neighbouring topics Organic reactions, so understanding it makes those chapters shorter.
In everyday life: Look for Thiol-yne reaction outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Thiol-yne reaction in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Thiol-yne reaction means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Thiol-yne reaction out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Thiol-yne reaction in simple terms?

Why does Thiol-yne reaction matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Thiol-yne reaction?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Thiol-yne reaction.