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Elimination of Alcohols To Alkenes With POCl3

by James

in Alcohols, Alkenes, Organic Chemistry 2

Heres what we talk about today: more eliminations of alcohols! Note that this reagent isnt covered in all
courses, but Ill include it here for completeness sake.
Weve talked about 2 ways to convert alcohols to alkenes so far:

Option #1: Convert the alcohol to an alkyl halide [with SOCl2, PBr3, or a hydrohalic acid] and then treat with a
strong base like NaOEt or similar to produce the alkene through an E2 process [2 operations]
Option #2: Heat the alcohol with a strong non-nucleophilic acid like H2SO4 or H3PO4 [1 operation]. [see post]

So which is better? Well, actually they both have their drawbacks.

Converting an alcohol to an alkyl halide followed by treatment with base is two separate operations. This is
OK, but it would be nice to be able to do this in one step.
Heating alcohols with strong acids is a one-step process, but can lead to carbocation rearrangements. Ideally
wed like to have better control of the products of these reactions, and avoid byproducts that come from hydride
or alkyl shifts.

Before we go any further, you might think this is nitpicky. You might think, two steps! Who cares!! Whats the
big deal? .

The big deal is we CARE about our time a lot! Think about how much you hate it when Facebook takes more
than 3 seconds to load. People will walk through a nicely manicured garden to shave five seconds off their
journey. Chemists are no different. If theres a way to do something in one step instead of two, well take it! So
yes, one step instead of two matters to us.

Today we talk about a process that gives us the best of both worlds a one-step process that proceeds under
much milder conditions than heating with acid.

It doesnt get covered in all introductory organic chemistry courses, but for completeness, well cover it here.

Direct Elimination of Alcohols To Alkenes With Phosphorus Oxychloride (POCl3)

As weve discussed before, hydroxide (HO- ) is a very poor leaving group. In order for alcohols to participate in
substitution and elimination reactions, its best to modify the oxygen in some way so as to be able to stabilize the
negative charge generated when the C-O bond breaks.

One way weve seen how to do this is by converting alcohols to alkyl sulfonates, such as tosylates or mesylates.
It would also work if we converted an alcohol to an alkyl phosphate [itself a good leaving group], but as it turns
out the OH groups on phosphate are acidic and can interfere with the basic reagents we typically use for
elimination. So a compromise is to use the reagent phosphorus oxychloride (POCl3), a derivative of phosphoric
acid. When POCl3 is added to an alcohol, we form a new O-P bond [the oxygen phosphorus bond is strong] and
break a P-Cl bond to form what we could call a chlorophosphate ester.

This is now a good leaving group! If we have a decent base around [such as pyridine] we can then get
elimination of this good leaving group to form a new alkene [via E2].

In practice an excess of pyridine is used here, or even use pyridine as the solvent.

Heres how it works:

This process proceeds in on operation, is much milder than heating an alcohol with strong acid and doesnt result
in rearrangements.

It works for primary, secondary, and tertiary alcohols.

Like I said it doesnt appear in all introductory courses but its important to know that when you see it, think
elimination. Importantly, dont confuse this reagent with PBr3 or PCl3 > those will convert an alcohol to
an alkyl halide, which is not the same reaction at all!

Next time

This is all well have to say about substitution and elimination reactions of alcohols, for now. In the next few
posts, well go through a special property of alcohols the ability of certain reagents to lead to their oxidation
to species such as aldehydes, ketones, and carboxylic acids. More next time!

Next Post: Alcohol Oxidation Strong and Weak Oxidants

Related Posts:

Elimination Reactions of Alcohols

Bulky Bases in Elimination Reactions
Introduction to Elimination Reactions
Guest Post on SN1/SN2/E1/E2 (4): The Electrophile

Tagged as: alkenes, dehydration, e2, elimination, pocl3

{ 5 comments read them below or add one }

PM

Ive seen some texts show SN2 at P of POCl3 and S of SOCl2. Clayden 2E (p 729 and p 214) are examples
of this. Is there any evidence for the presence of pentacoordinate phosphorus or sulfur intermediates in
these reactions? What are the pros and cons of each depiction?
 Reply

Dion Silverman

The addition of the alcohol to POCl3 is denoted as forming a chlorophosphite. Should this be a
chlorophosphate? If not, why not?

Thanks

Reply

James

Shoot, you are right. It should read, chlorophosphate.

Reply

tala

I love you. Best teacher EVER.

Reply

Thomas

Why POCl3 gives elimination and SOCl2 gives substitution? (Both reactions with same reagents..for
example a secondary alcohol and pyridine). In case of SOCl2, p
Can pyridine attack a beta H anyway?

Reply

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