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2
22.1. Organic chemistry is the study of carbon compounds
22.2. Hydrocarbons consist of only C and H atoms
22.3. Ethers and alcohols are organic derivatives of water
22.4. mines are organic derivatives of ammonia
22.!. Organic compounds with carbonyl groups include aldehydes" #etones" and carbo$ylic acids22.%. &olymers are composed of many repeating molecular
units
22.'. (ost biochemicals are organic compounds22.). *ucleic acids carry our genetic information
+nde$
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22.1. Organic chemistry is the study of carbon compounds 3
Organic Compounds re ,iverse
Carbon compounds are greatly variant due to the properties of C-
C is able to bond multiply
C is able to catenate
C is able to bond with a wide variety of elements
+somers are possible when there is a carbon chain
Combinations of functional groups give great diversity
Carbon can form rings
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22.1. Organic chemistry is the study of carbon compounds 4
Carbon Compounds
Carbon containing compounds e$ist in largevariety" mostly due to the multiple ways in which
C can form bonds
/ome groups of atoms with similar bonding are
commonly seen" called functional groups.
(olecules may contain more than one functional
group
Can form chiral compounds
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22.1. Organic chemistry is the study of carbon compounds !
0/E& /tructures
HC
CC
CC
H
H HH
HH
H H H
HH
/how all atoms
/how attachments between atoms but not how many
pairs of electrons were used
/how the geometric arrangement of the atoms
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22.1. Organic chemistry is the study of carbon compounds %
Condensed /tructures
CH3CH2CH2CH2CH3
show the general arrangement of the atoms and the
number of atoms
no effort is made to indicate geometry" types of bonds"
or lone pairs
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lcohols Ethers re &olar
Contain C" H" and O" all with single bonds. lcohols end in OH 5OH6
Ethers have an O atom in the chain 5O576
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8/8422.1. Organic chemistry is the study of carbon compounds )
8he Carbonyl 9roup
:hen C in a chain has a double bond to an o$ygen" thegroup is termed a carbonyl
ldehydes" #etones" carbo$ylic acids" and amides all
contain carbonyl groups
acidcarbo$ylic #etone aldehydeO ;
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9/8422.1. Organic chemistry is the study of carbon compounds =
ldehydes >etones re &olar
Each has a carbon chain terminating in a carbonyl. ldehydes then have an added H COH6
>etones have another carbon chain CO76
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mines mides re &olar
mines contain 5*H2 on carbon chain *H76 mides contain *H2 on carbon chain with
carbonyl CO*H26
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22.1. Organic chemistry is the study of carbon compounds 11
Carbo$ylic cids Esters re &olar
@oth have a carbon chain terminating in acarbonyl
Carboxylic acids then have an OH group
combined carbonyl and hydro$yl group form acarboxyl group COOH6
Esters then have a singly bound O" then another
carbon chain COO76
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22.1. Organic chemistry is the study of carbon compounds 13
Collecting molecules into families means that only
a few #inds of reactions must be learned
8he emphasis is on the properties of the functional
group" not individual molecules Once the center of reactivity is identified" its
characteristic reactions are e$pected to occur
Bsing Aunctional 9roups
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22.1. Organic chemistry is the study of carbon compounds 14
Aunctional 9roups nd 8heir &roperties
&olar functional groups contain O and * i#e dissolves li#e- polar solvents will dissolve
the polar functional groups
s the carbon chain increases in siDe" the polaritydecreases
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22.1. Organic chemistry is the study of carbon compounds 1!
our 8urnF
:hich of the followingcontains an amide
groupG
. 8he top structure
@. 8he middle
structure
C. 8he bottom
structure,. *one of these
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22.2. Hydrocarbons consist of only C and H atoms 1%
ewis /tructures Of Hydrocarbons
H C C C C C H
H
H
H
H
H
H
H
H
H
H
/how all atoms" and all electrons @ond pairs usually shown as a line
*on5bonding lone6 pairs of electrons are shown
as dots
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22.2. Hydrocarbons consist of only C and H atoms 1'
/tic# Aigures
Each verte$ and terminus is a carbon ssumes that the termini contain as many H as
needed for saturation of the C
hydrogens attached to hetero5atoms are shown6
ll hetero5atoms are shown e$plicitly
,ouble bonds e$plicitly shown
HC
CC
CC
H
H H H
HH
H H H
HH
CC
CC
C
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22.2. Hydrocarbons consist of only C and H atoms 1)
earning Chec#
Aill in the missing atoms and derive the condensedstructure
O
O
C!H12 C4H)O2
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22.2. Hydrocarbons consist of only C and H atoms 1=
our 8urnF
:hich is the correct formula for the structureshownG
. C42H12
@. C24H12C. C3%912
,. *one of these
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22.2. Hydrocarbons consist of only C and H atoms 21
l#anes CnH2n26
Composed of hydrocarbon chains in which carbonsare attached to one another by single bonds
re named by the number of C in the chain and
where any substitutions are found
&refi$es and the associated numbers of carbon
atoms
meth51 he$5%
eth52 hept57
prop53 oct5)
but54 non5=
pent5! dec51?
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22.2. Hydrocarbons consist of only C and H atoms 22
*aming l#anes
1. Aind the longest continuous chain of carbons5the root.
2. a. *ame the root by adding I5aneJ to the appropriate prefi$ a 45carbon chain would be butane6
b. +dentify any branches" and name each by thenumber of carbons a 15carbon branch is methyl56
3. a. ist side chains in alphabetical order" before theroot
b. Bse di" tri" tetra etcK6 if you have more than oneof something these do not count in alphabetiDing6
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22.2. Hydrocarbons consist of only C and H atoms 23
*aming Cont.6
4. *umber root from side closest to the first branch
!. Bse numbers to tell where the side chains
sprout from the root
%. &ut a dash between any number and letter or
any letter and number. Bse a comma between
two numbers
'. Bse the prefi$ IcycloJ for ring systems
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22.2. Hydrocarbons consist of only C and H atoms 24
*ame the following
35ethyl525methylhe$ane
35methylheptane
2"3"3"45tetramethylhe$ane
35ethyl545methylhe$ane
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22.2. Hydrocarbons consist of only C and H atoms 2!
our 8urnF
*ame the structure shown-. 1"25dimethylpentane
@. 35methylhe$ane
C. 25ethylpentane,. *one of these
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22.2. Hydrocarbons consist of only C and H atoms 2%
eactions Of l#anes
l#anes are generally stable at room temperature 8hey burn in air to given carbon dio$ide
:hen heated at high temperature they crack brea# into
smaller molecules6
ethene ethane
HCHCHCHCH
2HCCH
222
raturehigh tempe
33
2
raturehigh tempe
4
+= →
+ →
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22.2. Hydrocarbons consist of only C and H atoms 2'
Hydrocarbons with one or more double bonds are
members of the alkene family
open chain al#enes have the general formula C2H2n
Hydrocarbons with triple bonds are in the alkyne
family open chain al#ynes have the general formula" CnH2nL2
Bnsaturated Hydrocarbons
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22.2. Hydrocarbons consist of only C and H atoms 2)
*aming l#enes
8he parent chain must include the double bond 8he parent al#ene chain must be numbered from
whichever end gives the first carbon of the double
bond the lowest number
8his number" followed by a hyphen" precedes the
name of the parent chain" unless there is no
ambiguity about where the double bond occurs
8he locations of branches are not a factor innumbering the chain
l#yl groups are named and located as before
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22.2. Hydrocarbons consist of only C and H atoms 2=
*ame 8he Aollowing
ethylene 2"35dimethyl515pentene
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22.2. Hydrocarbons consist of only C and H atoms 31
9eometric +somers
Cis and trans isomers e$ist when thereis a plane of a double bond or of a
ring structure
cis same
trans5opposite
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22.2. Hydrocarbons consist of only C and H atoms 32
our 8urn
:hich isomer is shown-
. cis5
@. trans5
C. can7t tell
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22.2. Hydrocarbons consist of only C and H atoms 33
l#enes undergo addition reactions that eliminate the
pi5bond
CH2MCH2 HClg6 Cl5 CH25CH3
+norganic compounds that undergo addition reactions
with al#enes include- H2O" Cl2" @r 2" +2" and H2.
ODone O36 reacts with anything that has a carbon5
carbon double or triple bond" forming a variety of
products
ddition eactions of l#enes
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22.2. Hydrocarbons consist of only C and H atoms 34
romatic Compounds
Contain a benDeneC%H!56 ring with delocaliDedelectrons
romatic compounds undergo substitution reactionsinstead of addition reactions because of the
resonance energy of the ring e$ample- C%H% Cl2C%H!Cl HCl
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22.3. Ethers and alcohols are organic derivatives of water 3!
Ethers O76
esult when both hydrogen atoms in water arereplaced with al#yl groups
re almost as chemically inert as al#anes- they burn and are split apart when boiled in
concentrated acid re named by naming each al#yl group"
alphabetically" and end with IetherJ
earning Chec#-
CH3OCH3
CH3CH2OCH3
CH3CH2OCH2CH3
dimethyl ether ethyl methyl ether diethyl ether
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22.3. Ethers and alcohols are organic derivatives of water 3%
:hen an al#yl group replaces a hydrogen in water" an
alcohol results
8he name ending for alcohols is –ol
8he parent chain must include the carbon containing the
OH group earning Chec#- *ame the following
CH3CH2OH
CH3CH2CH2CH2OH
lcohols OH6
ethanol butanol
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22.3. Ethers and alcohols are organic derivatives of water 3'
+f the alcohol carbon atom holds at least one H atom" it
can be replaced with bonds to o$ygen
OH
O
CCHH
O
CCHOHCHCH
acidcarbo$ylic aldehyde alcohol
OH
O
C H
O
C OHCH
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22.3.Ethers and alcohols are organic derivatives of water 3)
8he IreverseJ the the addition of water to an
al#ene" it is an e$ample of an elimination
reaction
OHCHCHCHH
OH
CH
H
CCH 2232
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22.3. Ethers and alcohols are organic derivatives of water 3=
/ubstitution eactions Of lcohols
Bnder acidic conditions" the 5OH group can bereplaced by a halogen atom
ne bromopropa51 propanol51OH@r CHCHCHH@r4conc6OHCHCHCH 2223223
+→+
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22.3. Ethers and alcohols are organic derivatives of water 4?
our 8urnF
:hat type of structure is shown. lcohol
@. Ether
C. &ero$ide,. aldehyde
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22.4. mines are organic derivatives of ammonia 41
mines
re derivatives of ammonia where one or morehydrogens have been replaced with al#yl groups
*H3 is ammonia
CH3 *H2 is methylamine
CH362 *H is dimethylamine and CH363 * is
trimethylamine bp 3oC6.
mines are bases" and react with strong proton
donors to form ammonium ion5li#e structures
aN6 *HCHCHaN6HaN6 *HCHCH
aN6 *HaN6HaN6 *H
323223
43
++
++
→+
→+
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22.4. mines are organic derivatives of ammonia 42
re more soluble in water than amines
&rotonated amines li#e protonated ammonia6 are wea#
acids that can react with base
OHaN6 *HCHCHaN6OHaN6 *HCHCH
OHaN6 *HaN6OHaN6 *H
2223323
234
+→+
+→+
−+
−+
&rotonated mines
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22.!. Organic compounds with carbonyl groups include aldehydes" #e 43
8he +B&C name ending for an aldehyde is al
8he parent chain is the longest chain that includes
the aldehyde group
ldehydes
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22.!. Organic compounds with carbonyl groups include aldehydes" #e 44
>etones
8he +B&C ending for #etones is one.8he parent chain must include the
carbonyl group
propanone 35pentanone
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22.!. Organic compounds with carbonyl groups include aldehydes" #e 4!
eactions Of ldehydes >etones
ldehydes and #etones can be hydrogenated togive alcohols
ldehydes undergo o$idation to form
carbo$ylic acids" while #etones strongly resist
o$idation
propanol52 CHH
OH
CCHHCH
O
CCH
propanol51OHCHCHCHHH
O
CCHCH
3
<
323
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22.!. Organic compounds with carbonyl groups include aldehydes" #e 4%
Carbo$ylic cids
8he +B&C name ending for carbo$ylic acids is oic acid . the parent chain must include the
carbonyl carbon" which is numbered as position 1
8he common names are used for these- formic
acid and acetic acid
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22.!. Organic compounds with carbonyl groups include aldehydes" #e 4'
our 8urnF
:hich of the following contain a carbonyl groupG. amine
@. amide
C. carbo$ylic acid,. ll contain a carbonyl
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22.!. Organic compounds with carbonyl groups include aldehydes" #e 4=
Esters can be prepared by heating the parent acid with
an alcohol in the presence of an acid catalyst
ethanoateethyl ethanol acidethanoic
OHCHOCH
O
CCHCHCHHOCHOH
O
CCHCH
OHO;OC HO;OH
OC
232
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22.!. Organic compounds with carbonyl groups include aldehydes" #e !?
Carbo$ylic acids and alcohols can be obtained byheating esters with acid in a large e$cess of water
Esters are split apart by the action of base in a reaction
called saponification
ethanol ionethanoate
66
ethanoateethyl
66
23
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22.!. Organic compounds with carbonyl groups include aldehydes" #e !1
mides CO*H26
Carbo$ylic acids can also be converted into amides" afunctional group found in proteins
/imple amides are those in which the nitrogen bears
no al#yl groups" only hydrogen atoms
8he +B&C names of simple amides are generated by
replacing the oic acid of the parent carbo$ylic acid
with "amide
O
NH2
propanamide
O
H2N
25methyl5butanamide
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22.!. Organic compounds with carbonyl groups include aldehydes" #e !2
One way to prepare simple amides is by heatinga carbo$ylic acid in e$cess ammonia
e propanamid acid propanoic22
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22.!. Organic compounds with carbonyl groups include aldehydes" #e !3
mides" li#e esters" can be hydrolyDed
mides are not bases the O on the carbonyl draws
electron density to itself and ItightensJ the unshared
electrons on *" IpreventingJ their donation
acid propanoic e propanamid
3
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22.!. Organic compounds with carbonyl groups include aldehydes" #e !4
our 8urnF
:hich of these can be hydrolyDed react with water6. amides
@. al#anes
C. alcohols,. *one of these
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22.%. &olymers are composed of many repeating molecular units !!
&olymers
re large molecules with repeating units calledmonomers
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22.%. &olymers are composed of many repeating molecular units !%
Aormation Of ddition &olymers
Initiators attac# a monomer and ma#e it receptivefor the new bond
Addition polymers are assembled from molecular
units that combine to form one larger molecule
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22.%. &olymers are composed of many repeating molecular units !'
ddition &olymer- &olystyrene
/tyrene is treated with an initiator to form a freeradical
adical end is free to form a new connection to
another styrene molecule
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22.%. &olymers are composed of many repeating molecular units !)
Aormation Of Condensation &olymers
Condensation polymers are formed when monomersadd and lose a small molecule
adipic acid and he$amethylene diamine combine
and eliminate water to form *ylon %"%
8he ends are free to continue the process
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22.%. &olymers are composed of many repeating molecular units !=
Crosslin#ing
@ranches on polymersma#e them susceptible
to interaction with other
polymers
+ncreased crosslinking leads to increased
strength
8he concept behindvulcanized rubber
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22.%. &olymers are composed of many repeating molecular units %?
earning Chec#- 8eflon
+s formed from the monomer A2CPCA2 . @ased onthe structure of polytetrafluoroethylene &A8E6" is
this an addition or a condensation polymerG
addition
8h & l th l ,&E H,&E d
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22.%. &olymers are composed of many repeating molecular units %1
8he &olyethylenes- ,&E" H,&E and
BH(:&E
Have widely disparate properties due to the degree oforder
low density ,6 &E with anunordered crystal" is used for
grocery sac#s high density H,6 &E with
highly structured crystal isvery strong and used in80E>
ultra5high molecular weightBH(:6 &E has very longH,&E fibers and is used in bulletproof vests and sails
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22.%. &olymers are composed of many repeating molecular units %2
our 8urnF
One form of I9a#J can be made by combiningdissolved white glue and dissolved bora$
powder. :hat characteristics would you e$pect
if the amount of cross5lin#er the bora$6 is
increased in the blendG. +t becomes more viscous
@. +t becomes more solid
C. +t tears rather than stretches,. ll of the above
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22.%. &olymers are composed of many repeating molecular units %3
8he systematic study of the chemicals of living things variety of compounds are reNuired for cells to wor#-
lipids
carbohydrates
proteins
nucleic acids
@iochemistry
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22.'. (ost biochemicals are organic compounds %4
re naturally occurring polyhydro$yaldehydes or polyhydro$y#etones" or else compounds that react
with water to give these
8ypes-
monosaccharides
disaccharides
polysaccharides
Carbohydrates
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22.'. (ost biochemicals are organic compounds %!
(onosaccharides
re carbohydrates that do not react with water 8he most common monosaccharide is glucose
pentahydro$yaldehyde6
glucose is the chief carbohydrate in blood" and provides
a building units for polysaccharides li#e cellulose andstarch
OHOH
OH
OH
O
OH
CHCH
CH
CH CH
C
H2
O
CH
C
HC
HC
HC
HCH2
OH
OH
OH
OH
OH
glucose open chain polyhydro$yaldehyde6 Q5glucose
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22.'. (ost biochemicals are organic compounds %%
,isaccharides
re carbohydrates that split into twomonosaccharide molecules by reacting with water
e$ample- sucrose table sugar" cane sugar" or beet
sugar6 which gives glucose and fructose upon
hydrolysis
l h id
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22.'. (ost biochemicals are organic compounds %'
re naturally occurring polymers whose moleculesinvolve thousands of monosaccharide units lin#ed to
each other by o$ygen bridges
include starch" glycogen" and cellulose 5all give only
glucose upon hydrolysis plants store energy as starch
the hydrolysis of amylose the simplest starch6 can be
represented as-
large6isnamylose
glucose6 2 nOnH OH %luO%lu n →+−−−
&olysaccharides
/ f l
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22.'. (ost biochemicals are organic compounds %)
nimals store glucose for energy as glycogen e$cess glucose is converted to glycogen by liver and
muscle cells and stored for later use
Cellulose" a chief component of plant cell walls"
is a polymer of glucose that reNuires a specialenDyme to hydrolyDe
humans lac# this enDyme and so are unable to use
cellulose for food
cellulose is the IfiberJ found in foods li#e lettuce
/torage of glucose
i id
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22.'. (ost biochemicals are organic compounds %=
re fats and oils that are non5polar" so they do notdissolve in water
re amphipathic-
the purely hydrocarbon5li#e portions the long groups
contributed by the fatty acids6 avoid water and are
called hydrophobic or Iwater fearingJ
the polar heads are hydrophilic or Iwater loving
ipids
8 i l l l
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22.'. (ost biochemicals are organic compounds '?
8riacylglycerols
re esters between glycerol and includeedible fats and oils li#e olive oil" butterfat"
and lard
re called vegetable oils when derived
from plants and animal fats when derivedfrom animals" and are made from fatty
acids
re said to be polyunsaturated vegetable
oils tend to have more al#ene double
bonds per molecule than animal fats
9l h h li id
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22.'. (ost biochemicals are organic compounds '1
8he lipids involved in animal cell membrane are called glycerophospholipids
8he lipid molecules of animal cell membranes are organiDed as a bilayer.
9lycerophospholipids
8 F
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22.'. (ost biochemicals are organic compounds '2
our 8urnF
:hich are forms of fatsG. ipids
@. 9lycerols
C. &olysaccharides
,. ll of these
& t i
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22.'. (ost biochemicals are organic compounds '3
&roteins
8he dominant structural units of proteins aremacromolecules called polypeptides
polypeptides are made from a set of about 2?
monomers called amino acids
polypeptides are copolymers of the amino acids
ti f & t i
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22.'. (ost biochemicals are organic compounds '4
8he final shape of a protein" called its native form" is critical to its ability to function
&hysical agents such as heat" poisons" and certain
solvents can alter a proteins native form when this happened the protein is said to have been
denatured
Enzymes are the catalysts in living cells
0irtually all enDymes are proteins
eactions of &roteins
* l i id
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22.). *ucleic acids carry our genetic information '!
Carry the geneticcode
re made of amino
acids
*ucleic cids
ti f ,*
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22.). *ucleic acids carry our genetic information '%
8he best hydrogen bonds are formed when the base pairs that ma#eup the bac#bone ImatchJ
denine 6 pairs with thymine 86" cytosine C6 pairs with
guanine 96" etc
,* replicates itself by splitting the IparentJ ,*
double heli$ and assembling the matching base pairs
on each strand
8he result is two IdaughterJ ,* double heli$es
eactions of ,*
li ti f ,*
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22.). *ucleic acids carry our genetic information ''
eplication of ,*
,* Ch t i ti
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22.). *ucleic acids carry our genetic information ')
single human gene has between 1??? and3??? bases
the bases do not occur continuously on a ,*
molecule
the separated segments of a ,* chain that ma#e upa gene are called exons because that unit helps to
e& press a message
the sections of ,* between the e$ons are called
introns because they are units that int errupt the gene
,* Characteristics
&reparation of &olypeptides
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22.). *ucleic acids carry our genetic information '=
Each polypeptide in a cell is made under the directionof its own gene
8he production of a polypeptide can be represented as-
Transcription- the genetic message is read off in the cellnucleus and transferred to ribonucleic acid *6
Translation- the genetic message" now on * outside thenucleus" is used to direct the synthesis of a polypeptide
e polypeptid*,* ntranslatioiontranscript → →
&reparation of &olypeptides
*
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22.). *ucleic acids carry our genetic information )?
Aour types of * are involved in the connection ofthe gene to the polypeptide
ribosomal RA or r* is pac#ed together with enDymes
in ribosomes! the manufacturing stations for polypeptides.
messenger RA or m* brings the blueprints for particular polypeptide to the manufacturing station
ribosome6
heterogeneous nuclear RA or hn* carries the
IprefabricatedJ parts amino acids6 to the ribosome
transfer RA or t5* carries amino acids to the
ribosomes
*
9enetic ,efects
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22.). *ucleic acids carry our genetic information )1
bout 2??? diseases are attributed to various#inds of defects in the genetic machinery of
cells
if a single base is wrong in a gene" it could result in
a completely different polypeptide being produced" possibly with fatal conseNuences
tomic radiation and chemical agents can also
cause defects" possibly causing cancer
9enetic ,efects
0iruses
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22.). *ucleic acids carry our genetic information )2
0iruses are pac#ages of chemicals usuallyconsisting of nucleic acid and protein
8heir nucleic acid ta#es over the genetic
machinery in certain cells of the host tissues
causing them to manufacture more virus particles
8he host cell bursts" releasing the newly
manufactured viruses" which can infect more cells
0iruses
our 8urnF
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22.). *ucleic acids carry our genetic information )3
our 8urnF
How many types of * are there in a livingorganismG
. 1
@. 2
C. 3
,. 4
our 8urnF
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our 8urnF
How many types of ,* are there in a livingorganismG
. 1
@. 2
C. 3
,. 4