chemistry

Hydrovinylation

Hydrovinylation 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 Hydrovinylation rather than just read about it. In short: In organic chemistry, hydrovinylation is the formal insertion of an alkene into the C-H bond of ethylene (H2C=CH2): CH2=CHR + CH2=CH2 → CH3−CHR−CH=CH2 The more general reaction, hydroalkenylation, is the formal insertion of an alkene into the C-H bond of any terminal alkene. The reaction is catalyzed by metal complexes.

Key takeaways

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

Reference excerpt

In organic chemistry, hydrovinylation is the formal insertion of an alkene into the C-H bond of ethylene (H2C=CH2):

CH2=CHR + CH2=CH2 → CH3−CHR−CH=CH2 The more general reaction, hydroalkenylation, is the formal insertion of an alkene into the C-H bond of any terminal alkene. The reaction is catalyzed by metal complexes. A representative reaction is the conversion of styrene and ethylene to 3-phenybutene:

PhCH = CH 2 + CH 2 = CH 2 ⟶ H − CH 2 − CH ( Ph ) − CH = CH 2 {\displaystyle {\ce {PhCH=CH2}}+{\color {red}{\ce {CH2=CH2}}}\longrightarrow {\color {red}{\ce {H -}}}{\ce {CH2-CH(Ph)}}{\color {red}{\ce {-CH=CH2}}}}

Ethylene dimerization The dimerization of ethylene which gives 1-butene is another example of a hydrovinylation. In the Dimersol and Alphabutol Processes, alkenes are dimerized for the production of gasoline and for comonomers such as 1-butene. These processes operate at several refineries across the world at the scales of about 400,000 tons/year (2006 report). 1-Butene is amenable to isomerization to 2-butenes, which is used in olefin conversion technology to give propylene.

In organic synthesis The addition can be done highly regio- and stereoselectively, although the choices of metal, ligands, and counterions often play very important role. Many metals have also been demonstrated to form active catalysts, including nickel and cobalt. In a stoichiometric version of a hydrovinylation reaction, nucleophiles add to an electrophilic transition metal alkene complex, forming a C-C bond. The resulting metal alkyl undergoes beta-hydride elimination, liberating the vinylated product.

Hydroarylation Hydroarylation is again a special case of hydrovinylation. Hydroarylation has been demonstrated for alkyne and alkene substrates. An early example was provided by the Murai reaction, which involves the insertion of alkenes into a C-H bond of acetophenone. The keto group directs the regiochemistry, stabilizing an aryl intermediate.

When catalyzed by palladium carboxylates, a key step is electrophilic aromatic substitution to give a Pd(II) aryl intermediate. Gold behaves similarly. Hydropyridination is a similar reaction, but entails addition of a pyridyl-H bond to alkenes and alkynes.

See also Vinylation, the process of affixing a vinyl group

References

Worked examples

Example 1 — a first encounter with Hydrovinylation

Start with the simplest possible case. Write down what Hydrovinylation 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 Hydrovinylation 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 Hydrovinylation 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 Hydrovinylation

In research: Hydrovinylation 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 Hydrovinylation 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: Hydrovinylation is common in secondary-school and first-year university syllabi. It links to neighbouring topics Alkenes, Carbon-carbon bond forming reactions, so understanding it makes those chapters shorter.
In everyday life: Look for Hydrovinylation 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 Hydrovinylation in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Hydrovinylation 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 Hydrovinylation out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Hydrovinylation in simple terms?

In organic chemistry, hydrovinylation is the formal insertion of an alkene into the C-H bond of ethylene (H2C=CH2): CH2=CHR + CH2=CH2 → CH3−CHR−CH=CH2 The more general reaction, hydroalkenylation, is the formal insertion of an alkene into the C-H bond of any terminal alkene. The reaction is catalyz…

Why does Hydrovinylation 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 Hydrovinylation?

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 Hydrovinylation.