INTRODUCING HALOGENOALKANES

(haloalkanes or alkyl halides)

Halogenoalkanes are also known as haloalkanes or alkyl

halides. This page explains what they are and discusses their
physical properties. It also takes an initial look at their chemical
reactivity. Details of the chemical reactions of halogenoalkanes
are described on separate pages.

Fluoroalkanes are so unreactive that we shall mostly just ignore

them apart from pointing out why they are so unreactive.

What are halogenoalkanes?

Examples

Halogenoalkanes are compounds in which one or more

hydrogen atoms in an alkane have been replaced by halogen
atoms (fluorine, chlorine, bromine or iodine). For the purposes of
UK A level, we will only look at compounds containing one
halogen atom.

For example:

Note: If you aren't confident about naming organic compounds, then you
really ought to follow this link before you go on.

Use the BACK button on your browser to return to this page.

The different kinds of halogenoalkanes

Halogenoalkanes fall into different classes depending on how

the halogen atom is positioned on the chain of carbon atoms.
There are some chemical differences between the various types.
Primary halogenoalkanes

In a primary (1°) halogenoalkane, the carbon which carries the

halogen atom is only attached to one other alkyl group.

Note: An alkyl group is a group such as methyl, CH 3, or ethyl, CH3CH2.

These are groups containing chains of carbon atoms which may be
branched. Alkyl groups are given the general symbol R.

Some examples of primary halogenoalkanes include:

Notice that it doesn't matter how complicated the attached alkyl

group is. In each case there is only one linkage to an alkyl
group from the CH2 group holding the halogen.

There is an exception to this. CH3Br and the other methyl

halides are often counted as primary halogenoalkanes even
though there are no alkyl groups attached to the carbon with the
halogen on it.

Secondary halogenoalkanes

In a secondary (2°) halogenoalkane, the carbon with the halogen

attached is joined directly to two other alkyl groups, which may
be the same or different.

Examples:

Tertiary halogenoalkanes

In a tertiary (3°) halogenoalkane, the carbon atom holding the

halogen is attached directly to three alkyl groups, which may be
any combination of same or different.

Examples:
Physical properties of halogenoalkanes

Boiling Points

The chart shows the boiling points of some simple

halogenoalkanes.

Notice that three of these have boiling points below room

temperature (taken as being about 20°C). These will be gases at
room temperature. All the others you are likely to come across
are liquids.

Remember:

 the only methyl halide which is a liquid is iodomethane;

 chloroethane is a gas.

The patterns in boiling point reflect the patterns in intermolecular

attractions.

Note: If you aren't happy about intermolecular forces (particularly van der
Waals dispersion forces and dipole-dipole interactions) then you really
ought to follow this link before you go on.

Use the BACK button on your browser to return to this page.

van der Waals dispersion forces

These attractions get stronger as the molecules get longer and
have more electrons. That increases the sizes of the temporary
dipoles that are set up.

This is why the boiling points increase as the number of carbon

atoms in the chains increases. Look at the chart for a particular
type of halide (a chloride, for example). Dispersion forces get
stronger as you go from 1 to 2 to 3 carbons in the chain. It takes
more energy to overcome them, and so the boiling points rise.

The increase in boiling point as you go from a chloride to a

bromide to an iodide (for a given number of carbon atoms) is
also because of the increase in number of electrons leading to
larger dispersion forces. There are lots more electrons in, for
example, iodomethane than there are in chloromethane - count
them!

van der Waals dipole-dipole attractions

The carbon-halogen bonds (apart from the carbon-iodine bond)

are polar, because the electron pair is pulled closer to the
halogen atom than the carbon. This is because (apart from
iodine) the halogens are more electronegative than carbon.

The electronegativity values are:

C 2.5 F 4.0
Cl 3.0
Br 2.8
I 2.5

Note: If you don't understand about electronegativity and polar bonds

then you should follow this link before you go on.

Use the BACK button on your browser to return to this page.

This means that in addition to the dispersion forces there will be

forces due to the attractions between the permanent dipoles
(except in the iodide case).

The size of those dipole-dipole attractions will fall as the bonds

get less polar (as you go from chloride to bromide to iodide, for
example). Nevertheless, the boiling points rise! This shows that
the effect of the permanent dipole-dipole attractions is much less
important than that of the temporary dipoles which cause the
dispersion forces.

The large increase in number of electrons by the time you get to

the iodide completely outweighs the loss of any permanent
dipoles in the molecules.

Boiling points of some isomers

The examples show that the boiling points fall as the isomers go
from a primary to a secondary to a tertiary halogenoalkane. This
is a simple result of the fall in the effectiveness of the dispersion
forces.

The temporary dipoles are greatest for the longest molecule.

The attractions are also stronger if the molecules can lie closely
together. The tertiary halogenoalkane is very short and fat, and
won't have much close contact with its neighbours.

Solubility of halogenoalkanes

Solubility in water

The halogenoalkanes are at best only very slightly soluble in

water.

In order for a halogenoalkane to dissolve in water you have to

break attractions between the halogenoalkane molecules (van
der Waals dispersion and dipole-dipole interactions) and break
the hydrogen bonds between water molecules. Both of these
cost energy.

Note: If you aren't sure about hydrogen bonds, then you should follow
this link before you go on.

Use the BACK button on your browser to return to this page.

Energy is released when new attractions are set up between the
halogenoalkane and the water molecules. These will only be
dispersion forces and dipole-dipole interactions. These aren't as
strong as the original hydrogen bonds in the water, and so not
as much energy is released as was used to separate the water
molecules.

The energetics of the change are sufficiently "unprofitable" that

very little dissolves.

Note: To be accurate, you also have to consider entropy changes when

things dissolve. If you don't yet know about entropy, don't worry about it!

Solubility in organic solvents

Halogenoalkanes tend to dissolve in organic solvents because

the new intermolecular attractions have much the same strength
as the ones being broken in the separate halogenoalkane and
solvent.

Chemical reactivity of halogenoalkanes

The importance of bond strengths

The pattern in strengths of the four carbon-halogen bonds are:

Notice that bond strength falls as you go from C-F to C-I, and
notice how much stronger the carbon-fluorine bond is than the
rest.

Note: You will find almost as many different values for bond strengths (or
bond enthalpies or bond energies) as there are different sources! Don't
worry about this - the pattern is always the same. This is why you have
got a chart here rather than actual numbers.
In order for anything to react with the halogenoalkanes, the
carbon-halogen bond has got to be broken. Because that gets
easier as you go from fluoride to chloride to bromide to iodide,
the compounds get more reactive in that order.

Iodoalkanes are the most reactive and fluoroalkanes are the

least. In fact, fluoroalkanes are so unreactive that we shall pretty
well ignore them completely from now on in this section!

The influence of bond polarity

Of the four halogens, fluorine is the most electronegative and

iodine the least. That means that the electron pair in the carbon-
fluorine bond will be dragged most towards the halogen end.

Looking at the methyl halides as simple examples:

The electronegativities of carbon and iodine are equal and so

there will be no separation of charge on the bond.

Note: In the diagram, " " (read as "delta") means "slightly" - so +

means "slightly positive". The larger the symbols, the more positive or
negative the atoms are intended to be.

If this isn't reasonably familiar to you, then you ought to have read the
page about electronegativity and polar bonds mentioned above!

Use the BACK button on your browser to return to this page.

One of the important set of reactions of halogenoalkanes

involves replacing the halogen by something else - substitution
reactions. These reactions involve either:

 the carbon-halogen bond breaking to give positive and

negative ions. The ion with the positively charged carbon
 atom then reacts with something either fully or slightly
negatively charged.
 something either fully or negatively charged attracted to
the slightly positive carbon atom and pushing off the
halogen atom.

You might have thought that either of these would be more

effective in the case of the carbon-fluorine bond with the quite
large amounts of positive and negative charge already present.
But that's not so - quite the opposite is true!

The thing that governs the reactivity is the strength of the bonds
which have to be broken. If is difficult to break a carbon-fluorine
bond, but easy to break a carbon-iodine one.

Note: You will find all of this discussed in detail in the mechanism section
of this site under nucleophilic substitution reactions. This link will take you
to the most relevant page, but you may also want to explore the rest of
the nucleophilic substitution menu.

Use the BACK button (or HISTORY file or GO menu) on your browser if
you want to return to this page later.

Questions to test your understanding

If this is the first set of questions you have done, please read the
introductory page before you start. You will need to use the BACK
BUTTON on your browser to come back here afterwards.

questions on the introduction to halogenoalkanes

answers

Where would you like to go now?

To the halogenoalkanes menu . . .

To the menu of other organic compounds . . .

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© Jim Clark 2003 (modified September 2015)

Haloalkane
From Wikipedia, the free encyclopedia

Tetrafluoroethane (a haloalkane) is a colorless liquid that boils well below room temperature
(as seen here) and can be extracted from common canned air canisters by simply inverting
them during use.

The haloalkanes (also known as halogenoalkanes or alkyl halides) are a group of chemical
compounds derived from alkanes containing one or more halogens. They are a subset of the
general class of halocarbons, although the distinction is not often made. Haloalkanes are
widely used commercially and, consequently, are known under many chemical and
commercial names. They are used as flame retardants, fire extinguishants, refrigerants,
propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce,
many halocarbons have also been shown to be serious pollutants and toxins. For example, the
chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a
controversial fumigant. Only haloalkanes which contain chlorine, bromine, and iodine are a
threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as
greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have
ozone-depleting properties and the United States Environmental Protection Agency has
designated the compound a non-ozone layer depleter. For more information, see
Halomethane. Haloalkane or alkyl halides are the compounds which have the general formula
"RX" where R is an alkyl or substituted alkyl group and X is a halogen (F, Cl, Br, I).

Haloalkanes have been known for centuries. Chloroethane was produced synthetically in the
15th century. The systematic synthesis of such compounds developed in the 19th century in
step with the development of organic chemistry and the understanding of the structure of
alkanes. Methods were developed for the selective formation of C-halogen bonds. Especially
versatile methods included the addition of halogens to alkenes, hydrohalogenation of alkenes,
and the conversion of alcohols to alkyl halides. These methods are so reliable and so easily
implemented that haloalkanes became cheaply available for use in industrial chemistry
because the halide could be further replaced by other functional groups.

While most haloalkanes are human-produced, non-artificial-source haloalkanes do occur on

Earth, mostly through enzyme-mediated synthesis by bacteria, fungi, and especially sea
macroalgae (seaweeds). More than 1600 halogenated organics have been identified, with
bromoalkanes being the most common haloalkanes. Brominated organics in biology range
from biologically produced methyl bromide to non-alkane aromatics and unsaturates (indoles,
terpenes, acetogenins, and phenols).[1][2] Halogenated alkanes in land plants are more rare, but
do occur, as for example the fluoroacetate produced as a toxin by at least 40 species of known
plants. Specific dehalogenase enzymes in bacteria which remove halogens from haloalkanes,
are also known.

Contents
 1 Classes
 2 Properties
 3 Occurrence
 4 Nomenclature
o 4.1 IUPAC
 5 Production
o 5.1 From alkanes
o 5.2 From alkenes and alkynes
o 5.3 From alcohols
o 5.4 From carboxylic acids
o 5.5 Biosynthesis
 6 Reactions
o 6.1 Substitution
 6.1.1 Mechanism
o 6.2 Elimination
o 6.3 Other
 7 Applications
 8 See also
 9 References

Classes
From the structural perspective, haloalkanes can be classified according to the connectivity of
the carbon atom to which the halogen is attached. In primary (1°) haloalkanes, the carbon that
carries the halogen atom is only attached to one other alkyl group. An example is
chloroethane (CH
3CH
2Cl). In secondary (2°) haloalkanes, the carbon that carries the halogen atom has two C–C
bonds. In tertiary (3°) haloalkanes, the carbon that carries the halogen atom has three C–C
bonds.

Haloalkanes can also be classified according to the type of halogen on group 7 responding to
a specific halogenoalkane. Haloalkanes containing carbon bonded to fluorine, chlorine,
bromine, and iodine results in organofluorine, organochlorine, organobromine and
organoiodine compounds, respectively. Compounds containing more than one kind of
halogen are also possible. Several classes of widely used haloalkanes are classified in this
way chlorofluorocarbons (CFCs), hydrochlorofluorocarbons (HCFCs) and
hydrofluorocarbons (HFCs). These abbreviations are particularly common in discussions of
the environmental impact of haloalkanes.

Properties
Haloalkanes generally resemble the parent alkanes in being colorless, relatively odorless, and
hydrophobic. Their boiling points are higher than the corresponding alkanes and scale with
the atomic weight and number of halides. This is due to the increased strength of the
intermolecular forces—from London dispersion to dipole-dipole interaction because of the
increased polarity. Thus carbon tetraiodide (CI
4) is a solid whereas carbon tetrafluoride (CF
4) is a gas. As they contain fewer C–H bonds, halocarbons are less flammable than alkanes,
and some are used in fire extinguishers. Haloalkanes are better solvents than the
corresponding alkanes because of their increased polarity. Haloalkanes containing halogens
other than fluorine are more reactive than the parent alkanes—it is this reactivity that is the
basis of most controversies. Many are alkylating agents, with primary haloalkanes and those
containing heavier halogens being the most active (fluoroalkanes do not act as alkylating
agents under normal conditions). The ozone-depleting abilities of the CFCs arises from the
photolability of the C–Cl bond.

Occurrence
Haloalkanes are of wide interest because they are widespread and have diverse beneficial and
detrimental impacts. The oceans are estimated to release 1-2 million tons of bromomethane
annually.[3]

A large number of pharmaceuticals contain halogens, especially fluorine. An estimated one

fifth of pharmaceuticals contain fluorine, including several of the most widely used drugs.[4]
Examples include 5-fluorouracil, fluoxetine (Prozac), paroxetine (Paxil), ciprofloxacin
(Cipro), mefloquine, and fluconazole. The beneficial effects arise because the C-F bond is
relatively unreactive. Fluorine-substituted ethers are volatile anesthetics, including the
commercial products methoxyflurane, enflurane, isoflurane, sevoflurane and desflurane.
Fluorocarbon anesthetics reduce the hazard of flammability with diethyl ether and
cyclopropane. Perfluorinated alkanes are used as blood substitutes.

Teflon structure

Chlorinated or fluorinated alkenes undergo polymerization. Important halogenated polymers

include polyvinyl chloride (PVC), and polytetrafluoroethene (PTFE, or Teflon). The
production of these materials releases substantial amounts of wastes.
Nomenclature
IUPAC

The formal naming of haloalkanes should follow IUPAC nomenclature, which put the
halogen as a prefix to the alkane. For example, ethane with bromine becomes bromoethane,
methane with four chlorine groups becomes tetrachloromethane. However, many of these
compounds have already an established trivial name, which is endorsed by the IUPAC
nomenclature, for example chloroform (trichloromethane) and methylene chloride
(dichloromethane). For unambiguity, this article follows the systematic naming scheme
throughout.

Production
Haloalkanes can be produced from virtually all organic precursors. From the perspective of
industry, the most important ones are alkanes and alkenes.

From alkanes

Main article: Free radical halogenation

Alkanes react with halogens by free radical halogenation. In this reaction a hydrogen atom is
removed from the alkane, then replaced by a halogen atom by reaction with a diatomic
halogen molecule. The reactive intermediate in this reaction is a free radical and the reaction
is called a radical chain reaction.

Free radical halogenation typically produces a mixture of compounds mono- or

multihalogenated at various positions. It is possible to predict the results of a halogenation
reaction based on bond dissociation energies and the relative stabilities of the radical
intermediates. Another factor to consider is the probability of reaction at each carbon atom,
from a statistical point of view.

Due to the different dipole moments of the product mixture, it may be possible to separate
them by distillation.

From alkenes and alkynes

In hydrohalogenation, an alkene reacts with a dry hydrogen halide (HX) like hydrogen
chloride (HCl) or hydrogen bromide (HBr) to form a mono-haloalkane. The double bond of
the alkene is replaced by two new bonds, one with the halogen and one with the hydrogen
atom of the hydrohalic acid. Markovnikov's rule states that in this reaction, the halogen is
more likely to become attached to the more substituted carbon. This is an electrophilic
addition reaction. Water must be absent otherwise there will be a side product of a
halohydrin. The reaction is necessarily to be carried out in a dry inert solvent such as CCl
4 or directly in the gaseous phase. The reaction of alkynes are similar, with the product being
a geminal dihalide; once again, Markovnikov's rule is followed.

Alkenes also react with halogens (X2) to form haloalkanes with two neighboring halogen
atoms in a halogen addition reaction. Alkynes react similarly, forming the tetrahalo
compounds. This is sometimes known as "decolorizing" the halogen, since the reagent X2 is
colored and the product is usually colorless and odorless.

From alcohols

Alcohol undergoes nucleophilic substitution reaction by halogen acid to give

Haloalkanes.Tertiary alkanol reacts with hydrochloric acid directly to produce tertiary
choloroalkane(alkyl chloride), but if primary or secondary alcohol is used, an activator such
as zinc chloride is needed. This reaction is exploited in the Lucas test.

The most popular conversion is effected by reacting the alcohol with thionyl chloride (SOCl
2) in the "Darzens halogenation," which is one of the most convenient laboratory methods
because the byproducts are gaseous. Both phosphorus pentachloride (PCl
5) and phosphorus trichloride (PCl
3) also convert the hydroxyl group to the chloride.

Alcohols may likewise be converted to bromoalkanes using hydrobromic acid or phosphorus

tribromide (PBr3). A catalytic amount of PBr
3 may be used for the transformation using phosphorus and bromine; PBr
3 is formed in situ.

Iodoalkanes may similarly be prepared using red phosphorus and iodine (equivalent to
phosphorus triiodide). The Appel reaction is also useful for preparing alkyl halides. The
reagent is tetrahalomethane and triphenylphosphine; the co-products are haloform and
triphenylphosphine oxide.

From carboxylic acids

Two methods for the synthesis of haloalkanes from carboxylic acids are the Hunsdiecker
reaction and the Kochi reaction.

Biosynthesis

Many chloro and bromolkanes are formed naturally. The principal pathways involve the
enzymes chloroperoxidase and bromoperoxidase.

By Rydons method

An alcohol on heating with halogen in presence of triphenyl phosphate produces haloalkanes

or alkyl halides.

Reactions
Haloalkanes are reactive towards nucleophiles. They are polar molecules: the carbon to
which the halogen is attached is slightly electropositive where the halogen is slightly
electronegative. This results in an electron deficient (electrophilic) carbon which, inevitably,
attracts nucleophiles.

Substitution
Substitution reactions involve the replacement of the halogen with another molecule—thus
leaving saturated hydrocarbons, as well as the halogenated product. Haloalkanes behave as
the R+ synthon, and readily react with nucleophiles.

Hydrolysis, a reaction in which water breaks a bond, is a good example of the nucleophilic
nature of haloalkanes. The polar bond attracts a hydroxide ion, OH− (NaOH(aq) being a
common source of this ion). This OH− is a nucleophile with a clearly negative charge, as it
has excess electrons it donates them to the carbon, which results in a covalent bond between
the two. Thus C–X is broken by heterolytic fission resulting in a halide ion, X−. As can be
seen, the OH is now attached to the alkyl group, creating an alcohol. (Hydrolysis of
bromoethane, for example, yields ethanol). Reaction with ammonia give primary amines.

Chloro- and bromoalkanes are readily substituted by iodide in the Finkelstein reaction. The
iodoalkanes produced easily undergo further reaction. Sodium iodide is used thus as a
catalyst.

Haloalkanes react with ionic nucleophiles (e.g. cyanide, thiocyanate, azide); the halogen is
replaced by the respective group. This is of great synthetic utility: chloroalkanes are often
inexpensively available. For example, after undergoing substitution reactions, cyanoalkanes
may be hydrolyzed to carboxylic acids, or reduced to primary amines using lithium
aluminium hydride. Azoalkanes may be reduced to primary amines by the Staudinger
reduction or lithium aluminium hydride. Amines may also be prepared from alkyl halides in
amine alkylation, the Gabriel synthesis and Delepine reaction, by undergoing nucleophilic
substitution with potassium phthalimide or hexamine respectively, followed by hydrolysis.

In the presence of a base, haloalkanes alkylate alcohols, amines, and thiols to obtain ethers,
N-substituted amines, and thioethers respectively. They are substituted by Grignard reagents
to give magnesium salts and an extended alkyl compound.

Mechanism

Where the rate-determining step of a nucleophilic substitution reaction is unimolecular, it is

known as an SN1 reaction. In this case, the slowest (thus rate-determining step) is the
heterolysis of a carbon-halogen bond to give a carbocation and the halide anion. The
nucleophile (electron donor) attacks the carbocation to give the product.

SN1 reactions are associated with the racemization of the compound, as the trigonal planar
carbocation may be attacked from either face. They are favored mechanism for tertiary
haloalkanes, due to the stabilization of the positive charge on the carbocation by three
electron-donating alkyl groups. They are also preferred where the substituents are sterically
bulky, hindering the SN2 mechanism.

Elimination

Main article: Dehydrohalogenation

Rather than creating a molecule with the halogen substituted with something else, one can
completely eliminate both the halogen and a nearby hydrogen, thus forming an alkene by
dehydrohalogenation. For example, with bromoethane and sodium hydroxide (NaOH) in
ethanol, the hydroxide ion HO− abstracts a hydrogen atom. Bromide ion is then lost, resulting
in ethylene, H2O and NaBr. Thus, haloalkanes can be converted to alkenes. Similarly,
dihaloalkanes can be converted to alkynes.

In related reactions, 1,2-dibromocompounds are debrominated by zinc dust to give alkenes

and geminal dihalides can react with strong bases to give carbenes.

Other

Haloalkanes undergo free-radical reactions with elemental magnesium to give

alkylmagnesium compounds: Grignard reagents. Haloalkanes also react with lithium metal to
give organolithium compounds. Both Grignard reagents and organolithium compounds
behave as the R− synthon. Alkali metals such as sodium and lithium are able to cause
haloalkanes to couple in the Wurtz reaction, giving symmetrical alkanes. Haloalkanes,
especially iodoalkanes, also undergo oxidative addition reactions to give organometallic
compounds.

Applications
Haloalkanes are widely used as synthon equivalents to alkyl cation (R+) in organic synthesis.
They can also participate in a wide variety of other organic reactions.

Short chain haloalkanes such as dichloromethane, trichloromethane (chloroform) and

tetrachloromethane are commonly used as hydrophobic solvents in chemistry. They were
formerly very common in industry; however, their use has been greatly curtailed due to their
toxicity and harmful environmental effects.

Chlorofluorocarbons were used almost universally as refrigerants and propellants due to their
relatively low toxicity and high heat of vaporization. Starting in the 1980s, as their
contribution to ozone depletion became known, their use was increasingly restricted, and they
have now largely been replaced by HFCs.

Bromochlorodifluoromethane (Halon 1211), and Bromotrifluoromethane (Halon 1301), as

well as others are used in fire extinguishers. Due to their high ozone depletion potential,
production has ended as of April 6, 1998[5] cost is high, and they are primarily used for
critical applications such as aviation[5] and military.

See also
 Halogenation
 Halomethane
 Halogenoarene
 Halon (disambiguation)

References
1.
 Butler, Alison; Catter-Facklin, Jayen M. (2004). "The role of vanadium bromoperoxidase
in the biosynthesis of halogenated marine natural products". Natural Product Reports. 21
(1): 180–188. PMID 15039842. doi:10.1039/b302337k.
  Winter JM, Moore BS (2009). "Exploring the chemistry and biology of vanadium-
dependent haloperoxidases (Review of vanadium-dependent bromoperoxidases in nature)". J
Biol Chem. 284 (28): 18577–81. PMC 2707250  . PMID 19363038.
doi:10.1074/jbc.R109.001602.
  Gordon W. Gribble (1998). "Naturally Occurring Organohalogen Compounds". Acc.
Chem. Res. 31 (3): 141–152. doi:10.1021/ar9701777.
  Ann M. Thayer (June 5, 2006). "Fabulous Fluorine". Chemical and Engineering News.
84: 15–24.

5.  "Aviation requirements for fire extinguishers". Retrieved 17 December 2014.

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
MAKING HALOGENOALKANES
(haloalkanes or alkyl halides)

This page looks at ways of making halogenoalkanes in the lab

starting from alcohols. It covers more than enough detail for UK
A level purposes, but isn't intended to be all-inclusive!

Summarising the methods of preparation

Halogenoalkanes can be made from the reaction between

alkenes and hydrogen halides, but they are more commonly
made by replacing the -OH group in an alcohol by a halogen
atom. That's the method we'll concentrate on in this page.

Making halogenoalkanes from alcohols using hydrogen

halides

The general reaction looks like this:

Making chloroalkanes

It is possible to make tertiary chloroalkanes successfully from

the corresponding alcohol and concentrated hydrochloric acid,
but to make primary or secondary ones you really need to use a
different method - the reaction rates are too slow.

A tertiary chloroalkane can be made by shaking the

corresponding alcohol with concentrated hydrochloric acid at
room temperature.

Note: If you don't know what primary, secondary and tertiary

halogenoalkanes are, you should read the introduction to
halogenoalkanes before you go on.

Use the BACK button on your browser to return to this page.

Making bromoalkanes

Rather than using hydrobromic acid, you usually treat the

alcohol with a mixture of sodium or potassium bromide and
concentrated sulphuric acid. This produces hydrogen bromide
which reacts with the alcohol. The mixture is warmed to distil off
the bromoalkane. You will find practical details of a reaction of
this kind further down the page.

Making iodoalkanes

In this case the alcohol is reacted with a mixture of sodium or

potassium iodide and concentrated phosphoric(V) acid, H3PO4,
and the iodoalkane is distilled off. The mixture of the iodide and
phosphoric(V) acid produces hydrogen iodide which reacts with
the alcohol.

Phosphoric(V) acid is used instead of concentrated sulphuric

acid because sulphuric acid oxidises iodide ions to iodine and
produces hardly any hydrogen iodide. A similar thing happens to
some extent with bromide ions in the preparation of
bromoalkanes, but not enough to get in the way of the main
reaction.

Note: If you are interested in the reactions between halide ions

and concentrated sulphuric acid you could follow this link. In the
present context, all you would need to do is read the beginning of
that page.

If you choose to follow this link, use the BACK button on your
browser to return to this page.

Making halogenoalkanes from alcohols using phosphorus

halides

Making chloroalkanes
Chloroalkanes can be made by reacting an alcohol with liquid
phosphorus(III) chloride, PCl3.

Note: The reason for choosing a slightly bigger alcohol as an

example rather than using ethanol is that chloroethane (which
would be formed with ethanol) is a gas, and the preparation would
have to be handled differently. 1-chloropropane (formed in this
equation) is a liquid.

They can also be made by adding solid phosphorus(V) chloride,

PCl5 to an alcohol.

This reaction is violent at room temperature, producing clouds of

hydrogen chloride gas. It isn't a good choice as a way of making
halogenoalkanes, although it is used as a test for -OH groups in
organic chemistry.

There are also side reactions involving the POCl3 reacting with
the alcohol.

Making bromoalkanes and iodoalkanes

These are both made in the same general way. Instead of using
phosphorus(III) bromide or iodide, the alcohol is heated under
reflux with a mixture of red phosphorus and either bromine or
iodine.

The phosphorus first reacts with the bromine or iodine to give

the phosphorus(III) halide.

These then react with the alcohol to give the corresponding

halogenoalkane which can be distilled off.
Making bromoethane in the lab

This is a simple example of an organic preparation, and is one

of the most commonly used in A level chemistry courses.

Warning! The method described below is NOT complete. It

deliberately avoids mentioning quantities and doesn't cover any of
the safety aspects of the preparation. You can find full details in
most organic practical books.

Making impure bromoethane

Concentrated sulphuric acid is added slowly with lots of shaking

and cooling to some ethanol in a flask. Care has to be taken
because a great deal of heat is produced when the two are
mixed, and there is a real risk of the ethanol boiling and spraying
concentrated sulphuric acid around.

Solid potassium bromide is then added to the mixture, and the

flask is connected to a condenser so that the bromoethane
formed can be distilled off.

Bromoethane has a low boiling point but is denser than water

and almost insoluble in it. To prevent it from evaporating, it is
often collected under water in a flask surrounded by ice.
Sometimes it is simply collected in a tube surrounded by ice
without any water.

The reaction flask is heated gently until no more droplets of

bromoethane collect.

Purifying the bromoethane

Impurities in the bromoethane include:

 hydrogen bromide (although most of that will dissolve in

the water if you are collecting the bromoethane under
water);
 bromine - from the oxidation of bromide ions by the
concentrated sulphuric acid;
 sulphur dioxide - formed when concentrated sulphuric
acid oxidises the bromide ions;
  unreacted ethanol;
 ethoxyethane (diethyl ether) - formed by a side reaction
between the ethanol and the concentrated sulphuric acid.

The purification sequence

Stage 1

If you have collected the bromoethane under water, transfer the

contents of the collection flask to a separating funnel. Otherwise,
pour the impure bromoethane into the separating funnel, add
some water and shake it.

Pour off and keep the bromoethane layer.

The water you discard will contain almost all of the hydrogen
bromide, and quite a lot of any bromine, sulphur dioxide and
ethanol present as impurities.

Stage 2

To get rid of any remaining acidic impurities (including the

bromine and sulphur dioxide), return the bromoethane to the
separating funnel and shake it with either sodium carbonate or
sodium hydrogencarbonate solution.

This reacts with any acids present liberating carbon dioxide and
forming soluble salts.

Separate and retain the lower bromoethane layer as before.

Stage 3
Now wash the bromoethane with water in a separating funnel to
remove any remaining inorganic impurities (excess sodium
carbonate solution, etc). This time, transfer the lower
bromoethane layer to a dry test tube.

Stage 4

Add some anhydrous calcium chloride to the tube, shake well

and leave to stand. The anhydrous calcium chloride is a drying
agent and removes any remaining water. It also absorbs
ethanol, and so any remaining ethanol may be removed as well
(depending on how much calcium chloride you use).

Stage 5

Transfer the dry bromoethane to a distillation flask and

fractionally distil it, collecting what distils over at between 35 and
40°C.

In principle, this should remove any remaining organic

impurities. In practice, though, any ethoxyethane (which is
perhaps the most likely impurity left at this stage) has a boiling
point very, very close to that of bromoethane. It is unlikely that
you will be able to separate the two.

If there is any ethanol left which hadn't been absorbed by the

calcium chloride, that would certainly be removed because its
boiling point is much higher.

What's left?

In my experience with A level students, virtually nothing if you

are working on a small scale!! Every time you go through a
purification stage, you inevitably lose some of what you are
trying to collect.

Questions to test your understanding

If this is the first set of questions you have done, please read the
introductory page before you start. You will need to use the BACK
BUTTON on your browser to come back here afterwards.

questions on making halogenoalkanes

answers
 Where would you like to go now?

To the halogenoalkanes menu . . .

To the menu of other organic compounds . . .

To Main Menu . . .

© Jim Clark 2003 (modified September 2015)

Alcohols (Alkanols)

1) Alcohol is the common name for the alcohol ethanol (ethyl alcohol), contained in alcoholic
beverages (spirits). See also alcoholic fermentation and spirits.

2) Chemical group of the Alkanols, which contain one or more hydroxyl groups in the
molecule, see scheme of alkanols.

From the chemical structure it has to be distinguish between primary alcohols (like methanol,
ethanol, 1-propanol, 1-butanol ...), secondary alcohols (like 2-propanol, 2-butanol ...) and
tertiary alcohols (like tert. butanol) as representatives with only one single hydroxyl group,
also called univalent alcohols. Primarily means that the C-atom that is connected with the
hydroxyl group has only one alkyl residue (rsp. none with methanol), with secondary
alcohols there are two alkyl residues and according to three alkyl residues with tertiary
alcohols. See scheme of alkanols.

Important connections with more than one hydroxyl groups are ethylenglycol (two OH-
groups = diol, a bivalent alcohol) and the glycerol (three OH-groups = triol, a trivalent
alcohol). With diols, whose hydroxyl groups are bound at asymmetrically substituted carbon
atoms, spatially different arrangements exist, which are called as chirale isomers,. These
possesses a great importance to the purposeful synthesis of optically active natural
substances, which are often physiologically effective only in a defined stereochemistry. See
scheme of alkanols and alcohol database.

The nomenclature of the alcohols results from the name of the basis hydrocarbon,attaching
the ending "-ol". If different isomers are possible, the position of the OH-group (hydroxyl
group) is indicated by placing in front Arabic numerals. Chirale centers are represented by
placing the position as Arabic numeral and the optical direction of rotation in front,
 designation by the letters R rsp. S, in round parentheses (example: (2S, 5S)-2,5-Hexandiol).
See scheme of alkanols.

By the polarity of the hydroxyl group the formation of hydrogen bonds is possible. Therefore
melting and boiling points of the alcohols are clearly increased and the solubility of the short-
chained alcohols in polar solvents - especialy water - conditionally opposite the appropriate
alkanes, which decreases with increasing length of the hydrocarbon chain.

Synthesis of the alcohols

The synthesis of the primary and secondary alcohols under maintaining the carbon chain can
take place via reduction of the aldehydes rsp. ketones. The reduction of prochiralic ketones
with NADH (by means of alcohol and ADH regenerates in situ) permits the representation of
optically active alcohols, which are important parent compounds for the pharmaceutical
industry. Secondary and tertiary alcohols can be received by water addition to alkenes. A
general possible synthesis procedure under simultaneous extension of the hydrocarbon chain
offers the Grignard procedure. See synthesis.

Phenols

Substances which contain the hydroxyl group bound at an aromatic ring system doesn't
belong to the alcohols. This chemical substance class is called phenols, which are higher
reactive than alcohols because of more acid like behavior of the phenolic hydroxyl group.

Alcoholism Encyclopedia Alcopops

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ols are organic molecules containing only carbon (C), hydrogen (H) and oxygen (O)

ols belong to the group of organic compounds known as alcohols.

ols are hydroxy compounds, they contain an OH, hydroxy (or hydroxyl)1, functional

ght-chain alkanol consists of a chain of 1 or more carbon atoms joined to each other
gle covalent bonds, with an OH functional group attached to one of the carbon atoms
chain.
stematic IUPAC name2 of an alkan-n-ol is made up of three parts:

efix or stem
of parent hydrocarbon (the alkane chain) without the "e" ending, alkan)

infix
ber which tells us the location of the OH functional group, -n-)
Search this Si
uffix You can search this site using a key te
art of the name, ol) concept to find tutorials, tests, exams
activities (games).
ffix when naming a straight-chain alkanol is always "ol"
efix or stem is dependent on the number of carbon atoms in the longest chain of
atoms (the parent hydrocarbon, or parent alkane): Become an AU
f carbon TUTE Memb
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ms: AUS-e-TUTE members have access t
Centre containing:
x: meth eth prop but pent hex hept oct non dec
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Naming Straight Chain Alkanols
Teachers registered with a Class or Sc
y the longest carbon chain containing the OH (hydroxy or hydroxyl) functional can access the Teachers Only area:

 printable worksheets prepared

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mine the prefix for the name of the alkanol based on the number of carbon atoms in
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he parent alkane without the "e" ending) students
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er each carbon atom along the longest carbon chain so that the carbon atom bonded Find out more about AUS-e-TUTE M
droxy or hydroxyl) functional group has the lowest possible number.
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mine the infix for the name of the alkanol based on the location of the OH (hydroxy
unctional group.
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mine the suffix for the name of the alkanol. All straight chain alkanols containing
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the name for the alkanol in the form of prefix-infix-suffix

aming a Straight-Chain Alkanol AUS-e-TUTE's

ght chain alkanol shown below:
H H H
| | |
H- C - C - C - OH
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| | |
H H H
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y the longest carbon chain containing the OH (hydroxy or hydroxyl) functional
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n chain has 3 carbon atoms. to ask Chris, the AUS-e-TUTE

arbon is propane.

er each carbon atom along the longest carbon chain so that the carbon atom bonded
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numbered from right to left chain numbered from left to right

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| | | | | | AUS-e-TUTE tutorial topic
H- C - C - C1 - OH
3 2
H- C - C - C3 - OH
1 2

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n the chain.  Naming Simple Esters
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le, the OH group is attached to the first carbon atom in the chain, C1, so the infix is - Alkanamines
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mine the suffix for the name of the alkanol.
ain alkanols containing one OH (hydroxy or hydroxyl) functional group will end in

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Drawing the Structure3 of Straight Chain Alkanols Share this Pa

the systematic IUPAC name of the alkan-n-ol into its three parts:
alkan -n- ol
prefix infix suffix

nfix may be absent of the parent alkane chain contains only 1 or 2 carbon atoms.
mine the number of carbon atoms in the longest alkane carbon chain using the prefix.

a chain of carbon atoms of the required length using dashes to represent a single
between each pair of carbon atoms.

dashes around each carbon atom in the chain such that each carbon atom makes 4

er the carbon atoms in the chain from left to right.

mine the location of the OH (hydroxy or hydroxyl) functional group using the infix.
e is an OH functional group because the molecule's name has the suffix ol.

the OH group at the end of a dash on the carbon with the same number as the infix.

lete the structure by placing a hydrogen atom (H) at the end of all the vacant dashes.

rawing the Structure of a Straight-Chain Alkanol

re for the straight chain alkanol propan-2-ol (2-propanol or i-propyl alcohol).

the systematic IUPAC name of the alkan-n-ol into its three parts:

propan -2- ol
alkan -n- ol
prefix infix suffix

nfix may be absent of the parent alkane chain contains only 1 or 2 carbon atoms.

mine the number of carbon atoms in the longest alkane carbon chain using the prefix.
n
es the parent alkane chain is propane, a carbon chain containing 3 carbon atoms
valent bonds between each carbon atom in the chain.

a chain of carbon atoms of the required length using dashes to represent a single
between each pair of carbon atoms.

C-C-C

dashes around each carbon atom in the chain such that each carbon atom makes 4

| | |
-C-C-C-
| | |
er the carbon atoms in the chain from left to right.

| | |
- C - C - C3 -
1 2

| | |

mine the location of the OH (hydroxy or hydroxyl) functional group using the infix.
e is an OH functional group because the molecule's name has the suffix ol.

refore the OH group is attached to the second atom in the propane chain.

| | |
- C - C2 - C -
| | |

the OH group at the end of a dash on the carbon with the same number as the infix.

refore the OH group is attached to the second atom in the propane chain.

OH O-H
| | | | | |
2
OR 2
-C- C -C- -C- C -C-
| | | | | |

lete the structure by placing a hydrogen atom (H) at the end of all the vacant dashes.

H
H OH H |
| | | H O H
H- C - C - C -H OR | | |
| | | H- C - C - C -H
H H H | | |
H H H

Writing the Molecular Formula of Straight Chain

ormula tells us the number of atoms of each element present in a molecule of the

chain alkanol, only three elements are present, carbon (C), hydrogen (H) and oxygen
 the molecular formula of an alkanol, the number of carbon atoms is written before
hydrogen atoms which is written before the number of oxygen atoms, that is, C is
H which is written before O4:

CxHyO

the structure of the alkan-n-ol molecule.

a skeleton molecular formula using the symbols for carbon (C), hydrogen (H) and

CHO

the number of carbon atoms in the alkanol molecule.

the number of of carbon atoms into the skeleton molecular formula as a subscript
right of the symbol for carbon (C).

the number of hydrogen atoms in the alkanol molecule.

the number of of hydrogen atoms into the skeleton molecular formula as a subscript
right of the symbol for hydrogen (H).

the number of oxygen atoms in the alkanol molecule.

the number of of oxygen atoms into the skeleton molecular formula as a subscript
right of the symbol for oxygen (O).
y one hydroxy (or hydroxyl, OH) group is present, the number of oxygen atoms is 1,
ipt 1 is NOT included in the molecular formula.

that your completed molecular formula makes sense (CnH2n+2O)

Writing the Molecular Formula of a Straight-Chain Alkanols

ecular formula for butan-1-ol (1-butanol or n-butyl alcohol).

the structure of the alkan-n-ol molecule.

H H H H
| | | |
HO- C - C - C - C -H
| | | |
H H H H

a skeleton molecular formula using the symbols for carbon (C), hydrogen (H) and

CHO
 the number of carbon atoms in the alkanol molecule.

H H H H
| | | |
HO- C - C - C - C4 -H
1 2 3

| | | |
H H H H

the number of of carbon atoms into the skeleton molecular formula as a subscript
right of the symbol for carbon (C).

C4 H O

the number of hydrogen atoms in the alkanol molecule.

H2 H3 H4 H5
| | | |
1
HO- C - C - C - C -H6
| | | |
H H H H7
10 9 8

the number of of hydrogen atoms into the skeleton molecular formula as a subscript
right of the symbol for hydrogen (H).

C4H10O

the number of oxygen atoms in the alkanol molecule:

H H H H
| | | |
1
HO - C - C - C - C -H
| | | |
H H H H

the number of of oxygen atoms into the skeleton molecular formula as a subscript
right of the symbol for oxygen (O).
y one hydroxy (or hydroxyl, OH) group is present, the number of oxygen atoms is 1,
ipt 1 is NOT included in the molecular formula.

n atom is present in this molecule so no subscript 1 is required in the molecular

mula for butan-1-ol is C4H10O

 that your completed molecular formula makes sense (CnH2n+2O)
carbon atoms = 4
rogen atoms = 2 x n + 2 = 2 x 4 + 2 = 10
gen atoms = 1

Table: Molecular Formula, Structure and Name of

kanols
ms Molecular Formula
Structure Name
CnH2n+2O
H
|
CH4O H - C - OH methanol
|
H

H H
| |
ethanol
C2H6O H - C - C - OH
| | (ethan-1-ol)
H H

H H H
| | |
H - C - C - C - OH
propan-1-ol
| | | (1-propanol)
H H H
C3H8O H OH H
| | |
H-C-C -C-H
propan-2-ol
| | | (2-propanol)
H H H

H H H H
| | | |
H - C - C - C - C - OH
butan-1-ol
| | | | (1-butanol)
H H H H
C4H10O H H OH H
| | | |
H-C-C-C -C-H
butan-2-ol
| | | | (2-butanol)
H H H H

H H H H H
| | | | |
H - C - C - C - C - C - OH
pentan-1-ol
| | | | | (1-pentanol)
H H H H H
H H H OH H
C5H12O | | | | |
pentan-2-ol
H-C-C-C-C -C-H
| | | | | (2-pentanol)
H H H H H
H H OH H H pentan-3-ol
| | | | |
H-C-C-C -C-C-H (3-pentanol)
 | | | | |
H H H H H

H H H H H H
| | | | | |
H - C - C - C - C - C - C - OH
hexan-1-ol
| | | | | | (1-hexanol)
H H H H H H
H H H H OH H
| | | | | |
hexan-2-ol
C6H14O H-C-C-C-C-C -C-H
| | | | | | (2-hexanol)
H H H H H H
H H H OH H H
| | | | | |
H-C-C-C-C -C-C-H
hexan-3-ol
| | | | | | (3-hexanol)
H H H H H H

H H H H H H H
| | | | | | |
H - C - C - C - C - C - C - C - OH
heptan-1-ol
| | | | | | | (1-heptanol)
H H H H H H H
H H H H H OH H
| | | | | | |
H-C -C -C -C -C -C -C -H
heptan-2-ol
| | | | | | | (2-heptanol)
H H H H H H H
C7H16O H H H H OH H H
| | | | | | |
H-C -C -C -C -C -C -C -H
heptan-3-ol
| | | | | | | (3-heptanol)
H H H H H H H
H H H OH H H H
| | | | | | |
H-C -C -C -C -C -C -C -H
heptan-4-ol
| | | | | | | (4-heptanol)
H H H H H H H

H H H H H H H H
| | | | | | | |
H - C - C - C - C - C - C - C - C - OH
octan-1-ol
| | | | | | | | (1-octanol)
H H H H H H H H
H H H H H H OH H
| | | | | | | |
H-C -C -C -C -C -C-C -C-H
octan-2-ol
| | | | | | | | (2-octanol)
H H H H H H H H
C8H18O H H H H H OH H H
| | | | | | | |
H-C -C -C -C -C -C -C -C-H
octan-3-ol
| | | | | | | | (3-octanol)
H H H H H H H H
H H H H OH H H H
| | | | | | | |
H-C -C -C -C -C -C -C -C-H
octan-4-ol
| | | | | | | | (4-octanol)
H H H H H H H H
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roup in alkanols is called the hydroxy group or hydroxyl group.

ument refers to the hydroxy group, hydroxyl is also a possible name because of the retention of the unpaired electron on the

ossible name for the OH group because the "ide" suffix refers to the gain of an electron, that is, it refers to the negatively

er functional group takes precedence over the OH functional group, the OH group is then named as the hydroxy group.

iation for the International Union of Pure and Applied Chemistry

systematic name places the infix for the locant immediately before that part of the name to which it relates, except when the
me is the traditional contracted name in which case the infix is placed at the front of the name.
ht chain alkanols we are discussing, either nomenclature is acceptable since the name in each case is unambiguous.
C name is derived from a set of general "rules" designed to ensure that each organic molecule can be given an unambiguous

organic compounds are still being developed. The most recent document for referral is "Preferred names in the nomenclature
s" (Draft 7 October 2004).

refer to a valence structure, which can be used to represent the 2-dimensional structural formula.

the valence structure or 2-dimensional structural formula you can use this to draw

emi) structural formula

ucture

la of an alkanol is CnH2n+2O, while the often used CnH2n+1OH is, strictly speaking, not a molecular formula but a condensed

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