Presentation of the chemical properties of alcohols. Lesson topic: Lesson topic: Chemical properties of alcohols. Learning new material

Think and write it down! From the named substances: ethanediol, butanone, ethanol, propanal, propanetriol, 3-methylbutanol-1, choose: girls - polyhydric alcohols, boys - monohydric and make up their structural formulas. Checking: monohydric alcohols ethanol CH3-CH2-OH; 3-methylbutanol -1 CH3-CH-CH2-CH2-OH CH3 polyhydric alcohols ethanediol CH2 - CH2, propanetriol CH2 –CH –CH OH OH OH OH OH Part A










Establish a correspondence between the starting materials and the reaction products: 1. C2H5OH + Na H2SO4, t> 140 C 2. C2H5OH H2SO4, t 140 C 2. C2H5OH H2SO4, t "> 140 C 2. C2H5OH H2SO4, t"> 140 C 2. C2H5OH H2SO4, t "title =" (! LANG: Set the correspondence between the starting materials and the reaction products: 1. C2H5OH + Na H2SO4, t> 140 C 2.C2H5OH H2SO4, t"> title="Establish a correspondence between the starting materials and the reaction products: 1. C2H5OH + Na H2SO4, t> 140 C 2. C2H5OH H2SO4, t"> !}


140 CH OH 3. Esterification: CH3 – OH + CH3-CO-OH CH3 – CO-O-CH "title =" (! LANG: Alcohols are characterized by the following reactions: 1. Substitutions: 2C2H5OH + 2Na 2C2H5O– Na + H2 sodium ethylate 2. Dehydration: intermolecular and intramolecular H2SO4 CH3 CH CH2 CH3 CH = CH2 + H2O | | t> 140 CH OH 3. Esterification: CH3 – OH + CH3-CO-OH CH3 – CO-O-CH" class="link_thumb"> 8 !} Alcohols are characterized by the following reactions: 1. Substitutions: 2C2H5OH + 2Na 2C2H5O– Na + H2 sodium ethylate 2. Dehydration: intermolecular and intramolecular H2SO4 CH3 CH CH2 CH3 CH = CH2 + H2O | | t> 140 CH OH 3. Esterification: CH3 – OH + CH3-CO-OH CH3 – CO-O-CH3 + H2O methanol acetic acid methyl acetate 4. Oxidations: [O] [O] R – CH2 – OH R – CH = OR – СOOH -H2О aldehyde carboxylic acid 140 CH OH 3. Esterification: CH3 – OH + CH3-CO-OH CH3 – CO-O-CH "> 140 CH OH 3. Esterification: CH3 – OH + CH3-CO-OH CH3 – CO-O-CH3 + H2O methanol acetic acid methyl acetate 4. Oxidation: [O] [O] R – CH2 – OH R – CH = OR – COOH -H2O aldehyde carboxylic acid "> 140 CH OH 3. Esterification: CH3 – OH + CH3-CO-OH CH3 –CO-О-СН "title =" (! LANG: Alcohols are characterized by the following reactions: 1. Substitutions: 2C2H5OH + 2Na 2C2H5O– Na + H2 sodium ethylate 2. Dehydration: intermolecular and intramolecular H2SO4 CH3 CH CH2 CH3 CH = CH2 + H2O | | t> 140 CH OH 3. Esterification: CH3 – OH + CH3-CO-OH CH3 – CO-O-CH"> title="Alcohols are characterized by the following reactions: 1. Substitutions: 2C2H5OH + 2Na 2C2H5O– Na + H2 sodium ethylate 2. Dehydration: intermolecular and intramolecular H2SO4 CH3 CH CH2 CH3 CH = CH2 + H2O | | t> 140 C H OH 3. Esterification: CH3 – OH + CH3-CO-OH CH3 – CO-O-CH"> !}


The presence of oxidizing agents (heated copper (II) oxide, solutions of potassium dichromate and potassium permanganate) facilitates the reaction, and the hydrogen that is split off turns into water. t O CH 3 -CH 2 -OH + CuO CH 3 -C + Cu + H 2 OHK MnO 4 O CH 3 -CH 2 -OH CH 3 -C + H 2 OH 5. With hydrohalic acids CH3-CH2-OH + HBr = CH3-CH2-Br + H2O


Chemical properties of polyatomic alcohols: Acidic properties Substitution reactions Oxidation reactions Qualitative reaction Glycerin + Cu (OH) 2 bright blue coloration 1. Combustion 2. Oxidation of KMnO 4 1. Interaction with halogenides. 2. Esterification 1. Interaction with slit. metal. 2.With insoluble base










Conclusion: The number of hydroxyl groups affects the properties of alcohol (due to hydrogen bonds); The general properties with monohydric and polyhydric alcohols are due to the presence of the -OH functional group; Using the example of polyhydric alcohols, we are once again convinced that quantitative changes turn into qualitative changes: the accumulation of hydroxyl groups in the molecule caused, as a result of their mutual influence, the appearance of new properties in alcohols compared to monohydric alcohols - interaction with insoluble bases.


Homework. §37.3, repeat §37.1 and §37.2. Know the structural features and properties of alcohols, be able to draw up the reaction equations that characterize their properties. 4.9 in writing or prepare a presentation message "The use of monohydric and polyhydric alcohols" Additionally (part C) page

Classification of alcohols1
The nature
carbon
radical
2
3
In count
hydroxyl
groups
The nature
hydrogen atom,
which
bound
hydroxyl
group

Classification of alcohols
By the nature of the carbon radical
Title
ALCOHOLS
Add your text
CH3-CH2-CH2-OH
CH2-OH
Limit
Aromatic
CH2-CH-CH2-OH
Unlimited

R (OH) x
Alkanols
Alkenols
Alkinols
Phenols
Cycloalkonols
By the nature of the hydrocarbon radical with which it is associated
hydroxyl group the classification of alcohols is the same as
classification of hydrocarbons.

Classification of alcohols
by the number of hydroxyl groups
Title
ALCOHOLS
Add your text
CH2-CH-CH2-OH
I
I
I
OH OH OH
CH3-CH2-CH2
I
OH
Monatomic
(Ethanol)
CH2-CH-CH2-OH
I
I
OH OH
Diatomic
(Ethylene glycol)
Triatomic
(Glycerol)

Classification of alcohols
by the nature of the atom with which
linked hydroxyl group
Title
ALCOHOLS
Add your text
CH3-CH2-CH2
I
OH
Primary
(butanol - 1)
CH3-CH2-CH-OH3
CH3
I
CH3-C-CH3
I
OH
I
OH
Tertiary
(2-methylpropanol-2)
Secondary
(butanol - 2)

Methyl alcohol
CH3-OH - methanol
Ethanol
C2H5-OH - ethanol
Propyl alcohol
CH3-CH2-CH2-OH - propanol
Butyl alcohol
CH3-CH2-CH2-CH2-OH - butanol
Alkanols form a homologous series of the general formula
CnH2n + 1OH (n = 1,2,3,: N). The names of alkanols according to the systematic nomenclature are constructed from the names of the corresponding alkanes by adding the suffix "ol"

CH3-OH - methanol
C2H5-OH - ethanol

Isomerism of alcohols

Alkanols are characterized by two types of isomerism:
isomerism of the hydroxyl position
groups in the carbon chain
Alkanes
isomerism of the carbon skeleton.

Isomerism of the position of the hydroxyl group in the carbon chain

CH3-CH2-CH2-OH propanol
n-propyl alcohol
CH3-CH-CH
l
OH
propanol-2
(isopropyl alcohol)

CH3-CH2-CH2-CH2-OH butanol-1 (n-butyl alcohol)

Carbon skeleton isomerism
CH3-CH2-CH2-CH2-OH
butanol-1
(n-butyl alcohol)
CH3-CH-CH2-OH
l
CH3
2-methylpropanol-1
(isobutyl alcohol)
The first of the alcohols, which is characterized by
both isomerism, butanol is

Physical properties of alcohols

Alkanols are colorless liquids or crystalline
substances with a characteristic odor. The first members of the homologous
some have a pleasant smell, for butanols and pentanols smell
becomes unpleasant and annoying. Higher alkanols have
pleasant aromatic smell.

Boiling temperature

Boiling point of alcohols
Name of alcohol
Formula
Boiling temperature
Methyl (methanol)
CH3OH
64,7
Ethyl (ethanol)
С2Н5ОН
78,3
Propyl (propanol)
С3Н7ОН
97,2
Butyl (butanol-1)
С4Н9ОН
117,7
Amyl (pentanol-1)
С5Н11ОН
137,8

The high boiling point of alcohols is explained by
significant
intermolecular
interaction
–
association of molecules, the possibility of which is explained
polarity of the O – H bond and lone electronic
pairs of oxygen atoms. This interaction is called
hydrogen bonding

Ethanol molecule structure

N
N
δ-
Н – С – С
O
|
N
N
N
There are carbon atoms in the ethanol molecule,
hydrogen and oxygen are linked
only single links. Insofar as
electronegativity
oxygen is greater than the electronegativity of carbon and hydrogen,
common electronic pairs of bonds С–
O and O - H are shifted to the side
oxygen atom. It arises
partial negative, and on
atoms
carbon
and
hydrogen
partial positive charges.

Chemical properties of alcohols

Reactivity
alcohols due
presence in their molecules
polar bonds,
capable of bursting
on heterolytic
mechanism.
Alcohols exhibit weak
acid - base
properties

Types of reactions

Reactions
oxidation
Substitution reaction
hydrogen atoms
OH group
Substitution reaction
hydrogen atoms OH
group
Reaction
dehydration
(splitting off
water molecules)
Alkanols are characterized by
4 types of reactions:

Substitution reaction of hydrogen -OH group

С2Н5ОН + Na → C2H5ONa + H2
C2H5ONa + H2O → C2H5OH + NaOH
How weak acid alkanols can react with
alkali metals. The resulting
metal derivatives of alcohols are called
alcoholics.

Substitution reaction of –OH groups

The greatest practical value of the reactions of the second
type have reactions of substitution of a hydroxyl group by
halogens. This reaction can be carried out when
action on alkanols of various hydrohalic acids

Alkanol reactions
R - OH + H - X ↔ R - X + H2O
Reactivity of alkanols
R3С - OH> R2CH - OH> RCH2 - OH
Reactivity HX
HI> HBr> HCl >> HF
The reaction of alkanols with hydrohalic acids is
reversible. The efficiency of its flow depends on the structure
alkanol, nature of hydrogen halide and conditions.
The most active in this reaction are tertiary
alkanols and hydroiodic acid

Conducting reactions empirically

Dehydration reaction

Alkanols are characterized by two types of reaction
dehydration:
- intramolecular
and
- intermolecular
With intramolecular dehydration, alkenes are formed, with intermolecular dehydration, simple
ethers.

Intramolecular dehydration of alkanols
can be carried out by heating them with
an excess of concentrated H2SO4 at a temperature of 150-200 ° C or when passing alcohols
over heated solid catalysts.

Zaitsev's rule

CH3 - CH - CH - CH2
N
90%
CH2 - CH = CH - CH3
|
HE
N
100%
CH3 - CH2 - CH = CH2
Intramolecular
dehydration
asymmetrical
alkanols proceeds in accordance with the Zaitsev rule,
according to which hydrogen is split off mainly from
the least hydrogenated carbon atom and is formed
more stable alkene.

Dehydration of secondary alcohols

With the dehydration of secondary alcohols
maybe
the course of various rearrangements, leading to
obtaining an isomeric mixture of alkenes.

At weaker heating of ethyl alcohol with sulfuric acid
diethyl ether is formed. It is volatile, highly flammable.
liquid. Diethyl ether belongs to the class of ethers -
organic substances, the molecules of which consist of two
hydrocarbon radicals linked by an oxygen atom.
General formula R - O - R

Oxidation reactions

Oxidation of alcohols also occurs under the action of strong oxidants. Character
the products obtained in this case is determined by the degree
substitution of alcohols, as well as the nature of the used
oxidizer

Oxygenated organic substances, like
hydrocarbons, burn in air or oxygen with
the formation of water vapor and carbon dioxide. Combustion
alcohols is a highly exothermic reaction, therefore
they can be used as
high-calorie fuel.
CnH2n + 1OH + O2
nCO2 + (n + 1) H2O + Q

Oxidation of primary alcohols to carboxylic acids
proceeds with the action of HNO3 or potassium permanganate in
alkaline environment.
Oxidation of secondary alcohols leads to the formation
the corresponding ketones.

Oxidation of alcohols with copper oxide leads to the formation
aldehydes

Tertiary alcohols can only be oxidized under harsh conditions, when
the action of strong oxidants. Reactions are accompanied by rupture
C - C bonds at α-carbon atoms and the formation of a mixture
carbonyl compounds

Methanol and ethanol

Methanol is obtained by hydrogenation of carbon monoxide (II) CO. V
currently, a method has been developed for obtaining methanol by partial
recovery of carbon dioxide. In this case, more
cheap carbonaceous raw materials, but a large volume is required
hydrogen.
CO + 2H2
CO2 + 3H2
250-3500C, 5-30MPa
ZnO + ZnCr2O4
t0
cat
CH3OH
CH3OH + H2O

Application of individual representatives

Ethanol use

The most common method for producing ethanol
is the enzymatic cleavage of monosaccharides.
С6H10O5) n + nH2O
zymase
C6H12O6
2С2Н5OH + 2CO2

World production of methanol is about 10 million tons per year, ethanol
produced at about
order more. Methanol and
ethanol is used as
solvents and raw materials in organic synthesis. Moreover
ethanol is used in food
industry
and
v
medicine.

Remember

A hydrogen bond is a bond between an atom
hydrogen of one molecule and atoms with a large
electronegativity (O, F, N, Cl) of another molecule.
Esterification reaction - the interaction of alcohols with organic and inorganic acids
with the formation of esters.


  • Know the structure, nomenclature, physical and chemical properties of alcohols, their classification.
  • To be able to draw up formulas for isomers and homologues of alcohols, write reaction equations confirming the chemical properties of alcohols, give names by formulas.
  • Develop the ability to work with literature, analyze and draw conclusions.
  • To bring up independence, orderliness and orderliness.

  • By the number of hydroxyl groups.
  • By hydrocarbon radical
  • By the nature of the carbon atom bonded to the hydroxyl group

TERTIARY

SECONDARY

ONE BASIC

TWO-BASIC

PRIMARY

ALCOHOLS

THREE-BASIC

AROMATIC

UNMATCHED


  • Write down the names of the substances:
  • A) CH 3 - CH 2 - CHOH - CH 3
  • B) CH 3 - CH 2 - CH = CHON
  • A) butanol - 2
  • B) butene - 1 - ol - 1



  • interaction with alkali and alkaline earth metals.
  • Dehydration of alcohols a) intermolecular; b) intramolecular
  • Interaction with hydrogen halides
  • Interaction with acids (esterification reaction)
  • Oxidation of alcohols (qualitative reaction for alcohols)
  • Combustion of alcohols.

140º → c) CH 3 - OH + HBr → d) CH 3 - OH + O 2 → e) C 3 H 7 - OH + HCOOH → name the substances obtained: a) CH 3 –OH + Na → b) CH 3 OH Н 2 SO 4 (conc.) T ° c) С 3 Н 7 –ОН + HBr → d) С 3 Н 7 –ОН + О 2 → e) СН 3 ОН + С 2 Н 5 СООН → "width =" 640 "

Complete the following tasks

  • 1 OPTION
  • Name the substances:
  • A) CH 3 -CH 2 -OH
  • B) СН 3 –СН 2 –СНОН – СН 3
  • 2) Complete the possible reaction equations
  • OPTION 2
  • 1) Name the substances:
  • A) CH 3 –OH
  • B) СН 3 –СН 2 –СН 2 –СНОН – СН 3
  • 2) Finish the possible reaction equations, name the substances obtained:
  • a) С 3 Н 7 –ОН + К →
  • b) С 3 Н 7 - ОН Н 2 SO 4 (conc.) tº140º →
  • c) CH 3 - OH + HBr →
  • d) CH 3 - OH + O 2 →
  • e) С 3 Н 7 - ОН + НСООН →

name the substances obtained:

a) CH 3 –OH + Na →

  • b) СН 3 ОН Н 2 SO 4 (conc.) tº
  • c) С 3 Н 7 –ОН + HBr →
  • d) С 3 Н 7 –ОН + О 2 →
  • e) CH 3 OH + C 2 H 5 COOH →

Evaluation criteria

  • Count the number of points you earned per lesson. Give yourself a grade and report it to the teacher.
  • task: written down the definition of alcohols and the general formula -1 point; the scheme indicates 8 classes of alcohols for each of 0.5 points
  • all tasks are completed, the maximum number of points is 7, for an incorrect formula or its absence, an error in the name minus 0.5 points
  • All physical properties are recorded - 1 point, all chemical properties are recorded in general - 1 point, examples of reactions are given for each chemical property (7 equations for the example of ethyl alcohol) - 7 points, in total - 9 points for the task.
  • Independent work.
  • 1 task - 2 points
  • Task 2 - 5 points for the equations, 0.5 points each for the names of organic substances, 10 points in total.
  • RATINGS: 5 - IF YOU HAVE RECEIVED 25-31 POINTS;
  • 4 - IF YOU RECEIVED 19 - 24 POINTS;
  • 3 - IF YOU RECEIVED 15 - 23 POINTS;
  • 2 - IF YOU HAVE RECEIVED LESS THAN 15 POINTS.

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Slide captions:

Characteristics of alcohols. Development of a chemistry teacher MBOU Spasskaya secondary school G.V. Sudnitsina

Aims and objectives: to learn about the representatives of the class of alcohols, their classification, to study isomerism and the nomenclature of the class. Learn to solve test tasks on a topic.

Alcohols: classification, isomerism, nomenclature Alcohols are derivatives of hydrocarbons, in the molecules of which one or more hydrogen atoms are replaced by hydroxyl groups -OH. General formula of alcohols R- (OH) n

Alcohols Classification Monoatomic Diatomic Triatomic Methanol Ethanediol-1,2 (ethylene glycol) Propanetriol-1,2,3 (glycerin)

classification By the number of functional groups –OH Monatomic and polyatomic.

Alcohols Classification

Classification unsaturated aromatic alcohols By the nature of the hydrocarbon radical: C n H 2n + 1 OH C n H 2n-7 OH C n H 2n-1 OH

Saturated alcohols Unsaturated alcohols CH 2 = CH-OH CH 2 = CH-CH 2 -OH vinyl allyl Aromatic C 6 H 5 CH 2 OH benzyl alcohol phenol (Phenylmethanol)

Unsaturated monohydric alcohol is vitamin A, the most important biological function of which is participation in the visual process. And here is its formula:

Classification primary secondary tertiary alcohols By the type of binding of the hydroxyl group to the carbon atom:

Primary: CH 3 - CH 2 - OH, CH 3 - CH - CH 2 - OH CH 3 Secondary: CH 3 - CH - CH 3, CH 3 - CH 2 - CH - CH 3 OH OH Tertiary: CH 3 CH 3 - CH 2 - CH 2 - C - CH 3 OH

Alcohols Nomenclature and isomerism

isomerism Interclass isomerism ethanol CH 3 -CH 2 -OH and dimethyl ether CH 3 - O - CH 3

CH 3 CH 2 - O - CH 2 CH 3 Butanol-1 diethyl ether CH 3 -CH 2 -CH 2 -CH 2 - OH C 4 H 9 O Interclass isomerism

Find the formula for the isomer of butanol-1: Find the formulas for isomers and homologues:

Homologous series of saturated monohydric alcohols. Name of alcohols Boiling point formula (C 0) Methyl (methanol) CH 3 OH 64.7 Ethyl (ethanol) C 2 H 5 OH 78.3 Propyl (propanol-1) C 3 H 7 OH 97.2 Butyl (butanol-1 ) C 4 H 9 OH 117.7 Amyl (pentanol-1) C 5 H 11 OH 137.8 Hexyl (hexanol-1) C 6 H 13 OH 157.2 Heptyl (heptanol-1) C 7 H 15 OH 176, 3

nomenclature Pay attention to the peculiarities of the nomenclature of alcohols: The longest chain of carbon atoms is numbered from the end to which the hydroxyl group OH 6 5 4 I 3 2 1 CH3 - CH 2 - CH 2 - CH - CH 2 - CH 3 The basis of the name of alcohol is the name of the corresponding hydrocarbon with the addition of a suffix - ol Methanol, ethanol, propanol, butanol ...

The suffix is ​​followed by a number indicating the position of the hydroxyl group. propanol - 1, propanol - 2 ... At the same time, a rational nomenclature is also used for the names of some alcohols - methyl alcohol, ethyl alcohol, amyl ...

Formula 3-methylbutanol-2: 1 2 3 4

Test. Substances are given: 2-methylbutanol-2, pentanol-2, propylethyl ether, 2-methylbutanol-1, 2,2-dimethylpropanol-1. Find isomers of 1-pentanol and draw up structural formulas.

Alcohols Production methods Obtaining from alkenes

Alcohols Production methods Obtaining from halogen derivatives

Alcohols Production methods Obtaining from oxo compounds

Alcohols Physical properties CH 3 CH 2 OH Ethanol

Alcohols Physical Properties

... O - H ... O - H ... O - H ... O - H ... O - H ... O - H ... R R R R R R The first members of the homologous series of alcohols in comparison with the corresponding alkanes are liquids. This is due to the presence of hydrogen bonds between alcohol molecules. The bond between the hydrogen atom of one molecule and the atom of strongly electronegative elements (oxygen) of another molecule is called hydrogen

Alcohols Chemical properties Acid-base properties

Alcohols Chemical properties Acid-base properties or alcoholate

Intramolecular H 2 SO 4, t CH 3 - CH 2 - OH OH Intermolecular H 2 SO 4, t C 2 H 5 - OH + H O- C 2 H 5 OH H H + CH 2 = CH 2 + C 2 H 5 -O-C 2 H 5 Ethylene Diethyl ether

CH 3 –CH 2 - OH + CuO → CH 3 - C + Cu + H 2 O t 0 O H

Alcohols Chemical properties Nucleophilic substitution reactions Oxidation reactions

R - C + HO - RH 2 SO 4, t 0 O О H OH H Acid Alcohol Ester CH 3 –C О OH + H О C 2 H 5 ↔ CH 3 –СОО C 2 H 5 + H 2 О ethyl acetate ethyl ester acid alcohol acetic acid + R - C O - RO

Alcohols Chemical properties Substitution reactions Interactions of alcohols with halogen derivatives

Alcohols Chemical properties Nucleophilic substitution reactions Interactions of alcoholates with haloalkanes

Alcohols Chemical properties Nucleophilic substitution reactions

Cu (OH) 2 glycerin CH 2 - CH 2 OH OH ethylene glycol CH 2 - CH - CH 2 OH OH OH glycerin Qualitative reaction to polyhydric alcohols - interaction with a freshly prepared blue precipitate of copper hydroxide (+2) under normal conditions

1. WITH ALKALINE METALS GLYCOLS FORM COMPLETE AND INCOMPLETE GLYCOLATES: CH 2 OH CH 2 ONA 2 +2 NA 2 CH 2 OH CH 2 ONA

ETHYLENE GLYCOL REACTS WITH CORROSIVE ALKALIS: CH 2 OH CH 2 ONA +2 NAOH = + 2H 2 O CH 2 OH CH 2 ONA

Unlike monatomic alcohols, ethylene glycol readily interacts with copper (II) hydroxide, forming a bright blue copper glycol: H CH 2 OH CH 2 OO - CH 2 2 + Cu (OH) 2 2 Cu + 2H 2 O CHO - CH 2 H

WITH MINERAL AND ORGANIC ACIDS, THE COMPLETE AND INCOMPLETE ETHERS OBTAIN: + HONO 2 CH 2 ONO 2 H 2 O + CH 2 OH CH 2 OH CH 2 OH + 2HONO 2 CH 2 ONO 2 2H 2 O + CH 2 ONO 2

CHEMICAL PROPERTIES GLYCERIN IS VERY CLOSE TO ETHYLENE GLYCOL. SO, WITH COPPER (II) HYDROXIDE GLYCERINE FORMES A BRIGHT BLUE COPPER GLYCERATE: H CH 2 OH CH 2 -O O-CH 2 C O 2 CHOH + Cu -CH + 2H 2 OH CH 2 OH CH 2 -OH HO-CH 2 THIS IS A QUALITATIVE REACTION TO POLYATOMIC ALCOHOLS - ETHYLENE GLYCOL, GLYCERIN AND THEIR HOMOLOGIES.

When glycerol interacts with inorganic and organic acids, complete and incomplete esters are obtained. CH 2 OH CH 2 ONO 2 H 2 SO 4 2 CHOH + 3HNO 3 CHONO 2 +3 H 2 O CH 2 OH CH 2 ONO 2 NITROGLYCERINE IS A HEAVY OILY LIQUID, EXPLOSIVE (EXPLODES FROM GENTLY FRACTURE) AND HEAT.