01. Structure and properties of organic compounds. Aldehydes fnd keton..ppt

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About This Presentation

Structure and properties of organic compounds. Aldehydes fnd keton.


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LECTURELECTURE
CLASSIFICATION, STRUCTURE, CLASSIFICATION, STRUCTURE,
NOMENCLATURE AND NOMENCLATURE AND
PROPERTIES OF ORGANIC PROPERTIES OF ORGANIC
COMPOUNDS. COMPOUNDS.
TYPES OF CHEMICAL TYPES OF CHEMICAL REACTIONSREACTIONS
Lecturer: Iryna R. BekusLecturer: Iryna R. Bekus


Organic Chemistry Organic Chemistry – – tthe chemistry of he chemistry of
the hydrocarbons and their derivatives; the hydrocarbons and their derivatives;
the chemistry of carbon compounds.the chemistry of carbon compounds.

Bioorganic Chemistry Bioorganic Chemistry was study was study
structure and properties of compounds, structure and properties of compounds,
which are in human body. which are in human body.
Such as: Such as: proteins, lipids, hormones, carbohydrates, proteins, lipids, hormones, carbohydrates,
vitamins, enzyme, fatsvitamins, enzyme, fats, at el., at el.

CLASSIFICATIONCLASSIFICATION

By structure of carbon chain:By structure of carbon chain:

Acyclic Acyclic — — compounds, that don’t contain any compounds, that don’t contain any
cycle in their molecules. cycle in their molecules.
SaturatedSaturated — compounds that contain only — compounds that contain only --
bonds and nbonds and nоо  - bonds (simple – C – C – - bonds (simple – C – C –
bonds).bonds).
AlkanesAlkanes — saturated hydrocarbons that contain — saturated hydrocarbons that contain
only – C – C – and – C – H – only – C – C – and – C – H –  bonds. bonds.
UnsaturatedUnsaturated — compounds that contain — compounds that contain --
bonds and bonds and  - bonds (double bonds (– C = C –) - bonds (double bonds (– C = C –)
or triple (– C or triple (– C  C – ) bonds, and simple – C – C – ) bonds, and simple – C –
C – bonds).C – bonds).

AlkenesAlkenes — unsaturated hydrocarbons th— unsaturated hydrocarbons thааt t
contain only one – C – C – double bond contain only one – C – C – double bond
(– C = C –).(– C = C –).
DieneDiene — — unsaturatedunsaturated compounds compounds ththааt contain t contain
two double two double – C – C – – C – C – bonds.bonds.
AlkynesAlkynes — — unsaturatedunsaturated hydrocarbons hydrocarbons ththааt t
contain – C – C – contain – C – C – triple bond triple bond (– C (– C  C – ) C – )..
CyclicCyclic — organic compounds — organic compounds ththааt contain any t contain any
cycle in its molecules.cycle in its molecules.

CarbocyclicCarbocyclic - hydrocarbons containing - hydrocarbons containing аа cycle cycle
that consists of only Carbon atoms.that consists of only Carbon atoms.
CycloalkanesCycloalkanes — saturated hydrocarbons — saturated hydrocarbons
containing containing аа Carbon cycle. Carbon cycle.
CycloalkenesCycloalkenes — ansaturated hydrocarbons — ansaturated hydrocarbons
containing containing аа Carbon cycle. Carbon cycle.
ArenesArenes — aromatic compounds th— aromatic compounds thааt contain t contain
benzoic ring.benzoic ring.
HeterocyclicHeterocyclic - - organic compounds organic compounds ththааt contain t contain
cycle between atoms of Carbon and other cycle between atoms of Carbon and other
elements (S, O, N).elements (S, O, N).

Functional GroupFunctional Group is any is any
part of an organic part of an organic
compound, which is not compound, which is not аа
carbon-hydrogen or carbon-hydrogen or
carbon-carbon single bon.carbon-carbon single bon.

By functional groups:By functional groups:

There are mono-, poly- and heterofunctional group
in the structure of organic compounds:
Monofunctional group – contains only 1 functional group.
C
2H
5—OH
Polyfunctional group – contains several similar
functional group.
H
2C
CH
H
2C
OH
OH
OH
Heterofunctional group – contains several different functional
group.
OH
C
O
H

NOMENCLATURENOMENCLATURE

Common (trivial)Common (trivial)

International International ((IUPAC – IUPAC –
International Union of Pure International Union of Pure
and Applied Chemistryand Applied Chemistry ) )
system of nomenclature was first system of nomenclature was first
introduced in 1947.introduced in 1947.

General rules for IUPAC nomenclature:General rules for IUPAC nomenclature:

The The IUPACIUPAC name of any organic compound name of any organic compound
essentially consists of three parts: essentially consists of three parts:
1.1.word root; word root;
2.2.suffix; suffix;
3.3.prefix.prefix.

Thus, Thus, аа complete IUPAC name of an organic complete IUPAC name of an organic
compound consists of the following parts:compound consists of the following parts:
•Secondary prefix + Primary prefix + Word Secondary prefix + Primary prefix + Word
root + Primary suffix + Secondary suffixroot + Primary suffix + Secondary suffix

SUFFIXSUFFIX
There are two types of suffixes:There are two types of suffixes:

Primary suffix.Primary suffix. АА primary suffix is always primary suffix is always
added to the word root to indicate whether the added to the word root to indicate whether the
carbon chain is saturated carbon chain is saturated ооr unsaturated. The r unsaturated. The
three basic primary suffixes are given below:three basic primary suffixes are given below:


Secondary suffix.Secondary suffix. АА secondary suffix is then added secondary suffix is then added
to the primary suffix to indicate the nature of the to the primary suffix to indicate the nature of the
functional group present in the organic compound. functional group present in the organic compound.
Secondary suffixes of some important functional Secondary suffixes of some important functional
groups are given below:groups are given below:

PREFIXPREFIX
There are two types of prefixes:There are two types of prefixes:
Primary prefix.Primary prefix. АА primary prefix is primary prefix is
used simply to distinguish cyclic used simply to distinguish cyclic
from acyclic compounds.from acyclic compounds.
For example, in case of carbocyclic For example, in case of carbocyclic
compounds, compounds, аа primary prefix, cyclo primary prefix, cyclo
is used immediately before the is used immediately before the
word root. Thus:word root. Thus:

CyclopentaneCyclopentane

Secondary prefix.Secondary prefix. In IUPAC system of nomenclature, In IUPAC system of nomenclature,
certain groups are not considered as functional certain groups are not considered as functional
groups but instead are treated as substituents. These groups but instead are treated as substituents. These
are called secondary prefixes.are called secondary prefixes.

Complete structural formula:
C C C
H
H
H
H
H
H
H
C
H
H
H
C
C
C
C
C
C
H
H
H H
H
H
H
H
H
H
H
H
hexane butane

Shorten structural formula:
CH
3—CH
2—CH
2—CH
3
H
2
C
H
2C
H
2C
C
H
2
CH
2
CH
2
butane
hexane

Types of organic reactions.Types of organic reactions.
All the organic reactions can be broadly All the organic reactions can be broadly
classified into the following four types: classified into the following four types:

(a) substitution reactions, (a) substitution reactions,

(b) addition reactions, (b) addition reactions,

(c) elimination reactions, (c) elimination reactions,

(d) rearrangement reactions.(d) rearrangement reactions.

(I) (I) Substitution reactions which are brought about by Substitution reactions which are brought about by
nucleophiles are called nucleophiles are called nucleophilic substitution nucleophilic substitution
reactions:reactions:
CHCH
33
OH + CHOH + CH
33
COOH COOH  CH CH
33
COOCHCOOCH
33
+ H + H
22
OO
((II) II) Substitution reactions which are brought about by Substitution reactions which are brought about by
electropholes are called electropholes are called electrophilic substitution electrophilic substitution
reactionsreactions::
(III) (III) SubstitutionSubstitution reactions brought about by free reactions brought about by free
radicals are called radicals are called free free radical substitution radical substitution
reactionsreactions::
CHCH
44 +Cl +Cl
2 2 → → CHCH
33Cl +HClCl +HCl

Addition reactionsAddition reactions
Addition reactions are of the following three types:Addition reactions are of the following three types:
Addition reactions brought about by nucleophiles are called Addition reactions brought about by nucleophiles are called
nucleophilic addition reactionsnucleophilic addition reactions::
Addition reactions brought about by electrophiles are called Addition reactions brought about by electrophiles are called
electrophilic addition reactionselectrophilic addition reactions..
Addition reactions brought about by free radicals are called Addition reactions brought about by free radicals are called
free radical addition reactionsfree radical addition reactions..


Elimination reactions.Elimination reactions. An elimination reaction is An elimination reaction is
one that involves the loss of two atoms orgroups of one that involves the loss of two atoms orgroups of
atoms form the same or adjacent atoms of a atoms form the same or adjacent atoms of a
substance leading the formation of a multiple substance leading the formation of a multiple
(double or triple) bond: (double or triple) bond:
These are of two types:These are of two types:

-Elimination reactions-Elimination reactions..

-Elimination reactions.-Elimination reactions.

Reactions involving the migration of an atom or a group from Reactions involving the migration of an atom or a group from
one atom to another within the same molecule are called one atom to another within the same molecule are called
rearrangement reactions.rearrangement reactions.

OxidationOxidation — — аа net decrease in the number of net decrease in the number of 
bonds to hydrogen or electropositive element, or bonds to hydrogen or electropositive element, or аа
net increase in the number of bonds to net increase in the number of bonds to
electronegative elements. electronegative elements. АА net loss of electrons. net loss of electrons.
Reduction Reduction — — аа net increase in the number of net increase in the number of 
bonds to hydrogen or electropositive element, or bonds to hydrogen or electropositive element, or аа
net decrease in the number of bonds to net decrease in the number of bonds to
electronegative elements. electronegative elements. АА net gains electrons. net gains electrons.

ALCOHOL

In chemistry, an alcohol is an organic compound in
which the hydroxyl functional group (-OH) is bound
to a carbon atom. In particular, this carbon center
should be saturated, having single bonds to three
other atoms.

Systematic names
In the IUPAC system, the name of the alkane
chain loses the terminal "e" and adds "ol", e.g.,
"methanol" and "ethanol“

Classification of alcohols

Alcohols with one hydroxyl group - monohydric alcohol

Alcohols with two hydroxyl groups - dihydric alcohol

Alcohols with three hydroxyl groups - trihydric alcohols

Alcohols with four or more hydroxyl groups - polyhydric
alcohols

The saturated monohydric alcohols have the general
formula CnH2n+1OH or ROH. Their functional group
is -OH.
They can be further classified into:
1) Primary Alcohol
Here the carbon atom bearing the hydroxyl group is
attached to just one other carbon atom.
2) Secondary Alcohol
Here the carbon atom bearing the hydroxyl group is
attached to two other carbon atoms.

3)Tertiary Alcohol
Here the carbon atom bearing the hydroxyl group is
attached to three other carbon atoms.

Carbonyl GroupCarbonyl Group

Carbon atom joined to oxygen by a Carbon atom joined to oxygen by a
double bonddouble bond

KetonesKetones
Aldehydes
   
          
 
          

   
                                        
 
                                        

AldehydesAldehydes

Comes from alcohol dehydrogenationComes from alcohol dehydrogenation

Obtained by removing of a hydrogen Obtained by removing of a hydrogen
from an alcoholfrom an alcohol

   
                                                    
 
                                                    

Aldehydes Aldehydes

Both common and IUPAC names Both common and IUPAC names
frequently usedfrequently used

Common names from acids from Common names from acids from
which aldehydes can be convertedwhich aldehydes can be converted

   
                                                         
 
                                                         

AldehydesAldehydes

IUPACIUPAC

Longest chain with aldehydeLongest chain with aldehyde

Drop “e” and add “-al”Drop “e” and add “-al”
•Acetaldehyde Acetaldehyde PropionaldehydePropionaldehyde
Phenylethanal

KetonesKetones

Naming:Naming:
•Drop “e”, add “-one”Drop “e”, add “-one”
•Many common namesMany common names
•Simplest is 3 carbons Simplest is 3 carbons

C. name: acetoneC. name: acetone

IUPAC: propanoneIUPAC: propanone

   
                                                                    
 
                                                                    

Physical Properties of Aldehydes Physical Properties of Aldehydes
and Ketonesand Ketones

Carbon-oxygen double bond is very polarCarbon-oxygen double bond is very polar
•Affects boiling pointsAffects boiling points
•More than ethers (C-O bonds)More than ethers (C-O bonds)
•Less than alcohols (C-OH bonds)Less than alcohols (C-OH bonds)

OdorsOdors
•Low aldehydes very pungentLow aldehydes very pungent
•High aldehydes pleasant odors (perfumes)High aldehydes pleasant odors (perfumes)

Solubility Solubility
•Similar to alcohols and ethersSimilar to alcohols and ethers
•Soluble up to about 4 carbonsSoluble up to about 4 carbons
•Insoluble after thatInsoluble after that

Preparation of AldehydesPreparation of Aldehydes

Oxidation Oxidation

   
                                                                    
 
                                                                    
 
           
 
           

   
                                
 
                                
 
        
 
        

Hydration of alkynes (Kucherov reaction).
Reaction occurs by way of an enol
intermediate formed by Markovnikov
addition of water to the triple bond.

Oxosynthesis. Oxosynthesis.
Interaction of alkenes with carbone Interaction of alkenes with carbone
(II) oxide, at the higher temperature, (II) oxide, at the higher temperature,
pressure and presence of catalyst. pressure and presence of catalyst.

Preparation of KetonesPreparation of Ketones

OxidationOxidation

   
                    
 
                    
 
       
 
       

   
                      
 
                      
 
       
 
       

Chemical Properties of Aldehydes Chemical Properties of Aldehydes
and Ketonesand Ketones

Both undergo combustion reactionsBoth undergo combustion reactions

OxidationOxidation
•Aldehydes can be oxidized, ketones Aldehydes can be oxidized, ketones
can’tcan’t
•See See

Tollen’s reagentTollen’s reagent

Benedict’s reagentBenedict’s reagent

Fehling’s reagentFehling’s reagent
  

Reactions of aldehyde oxidationReactions of aldehyde oxidation

With Tollens’ reagent – “silver With Tollens’ reagent – “silver
mirror” reaction.mirror” reaction.
With Fehling reagent: after heating red
precipitate of copper (I) oxide formed.

Chemical Properties of Aldehydes Chemical Properties of Aldehydes
and Ketonesand Ketones

Reduction Reduction
•Variety of agents can reduce aldehydes Variety of agents can reduce aldehydes
and ketones to alcoholsand ketones to alcohols

   
                                 
 
                                 
 
        
 
        

   
                           
 
                           
 
       
 
       

   
                                                   
 
                                                   
 
          
 
          

Chemical Properties of Aldehydes Chemical Properties of Aldehydes
and Ketonesand Ketones

HydrationHydration
•Formaldehyde dissolves readily in waterFormaldehyde dissolves readily in water
•Acetaldehyde somewhat alsoAcetaldehyde somewhat also

Form Form hydrateshydrates
   
                              
 
                              
 
        
 
        

   
                           
 
                           
 
     
 
     

Chemical Properties of Aldehydes Chemical Properties of Aldehydes
and Ketonesand Ketones

Addition of Alcohols to Carbonyl Addition of Alcohols to Carbonyl
GroupsGroups
•HemiacetalHemiacetal

Aldehyde + alcoholAldehyde + alcohol
•Hemiketal Hemiketal

Ketone + alcoholKetone + alcohol

   
                            
 
                            
 
        
 
        

   
                            
 
                            
 
        
 
        

Chemical Properties of Aldehydes Chemical Properties of Aldehydes
and Ketonesand Ketones

Hemiacetals + HCl = acetalHemiacetals + HCl = acetal

Hemiketal + HCl = ketalHemiketal + HCl = ketal

   
                                                
 
                                                
 
          
 
          

Thank you for attentionThank you for attention
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