Ch22. Organic Compounds, Polymers,And Biochemicals

8/18/2019 Ch22. Organic Compounds, Polymers,And Biochemicals

1/84


2/84

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$


3/84

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


4/84


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


5/84

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


6/84

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


7/8422.1. Organic chemistry is the study of carbon compounds '

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


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 ;


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


10/8422.1. Organic chemistry is the study of carbon compounds 1?

mines mides re &olar

mines contain 5*H2 on carbon chain *H76 mides contain *H2 on carbon chain with

carbonyl CO*H26


11/84


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


12/84


13/84


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


14/84


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


15/84

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


16/84

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


17/84

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


18/84

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


19/84

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


20/84


21/84

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?


22/84


*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


23/84


*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


24/84


*ame the following

35ethyl525methylhe$ane

35methylheptane

2"3"3"45tetramethylhe$ane

35ethyl545methylhe$ane


25/84

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


26/84

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

+= →

+ →


27/84

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


28/84

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


29/84

22.2. Hydrocarbons consist of only C and H atoms 2=

*ame 8he Aollowing

ethylene 2"35dimethyl515pentene


30/84


31/84


9eometric +somers

Cis and trans isomers e$ist when thereis a plane of a double bond or of a

ring structure

cis same

trans5opposite


32/84


our 8urn

:hich isomer is shown-

. cis5

@. trans5

C. can7t tell


33/84


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


34/84


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


35/84

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


36/84

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


37/84

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


38/84

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


39/84

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

+→+


40/84

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


41/84

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

++

++

→+

→+


42/84

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


43/84

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


44/84

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


45/84

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


46/84

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


47/84

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


48/84


49/84

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


50/84

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


51/84

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


52/84


One way to prepare simple amides is by heatinga carbo$ylic acid in e$cess ammonia

e propanamid acid propanoic22


53/84


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


54/84


our 8urnF

:hich of these can be hydrolyDed react with water6. amides

@. al#anes

C. alcohols,. *one of these


55/84

22.%. &olymers are composed of many repeating molecular units !!

&olymers

re large molecules with repeating units calledmonomers


56/84

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


57/84

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


58/84

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


59/84

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


60/84

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


61/84

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


62/84


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


63/84


8he systematic study of the chemicals of living things variety of compounds are reNuired for cells to wor#-

lipids

carbohydrates

proteins

nucleic acids

@iochemistry


64/84

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


65/84

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


66/84

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


67/84

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


68/84

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


69/84

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


70/84

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


71/84

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


72/84


our 8urnF

:hich are forms of fatsG. ipids

@. 9lycerols

C. &olysaccharides

,. ll of these

& t i


73/84


&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


74/84


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


75/84

22.). *ucleic acids carry our genetic information '!

Carry the geneticcode

re made of amino

acids

*ucleic cids

ti f ,*


76/84

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 ,*


77/84

22.). *ucleic acids carry our genetic information ''

eplication of ,*

,* Ch t i ti


78/84

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


79/84

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

*


80/84

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


81/84

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


82/84


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


83/84


our 8urnF

How many types of * are there in a livingorganismG

. 1

@. 2

C. 3

,. 4

our 8urnF


84/84

our 8urnF

How many types of ,* are there in a livingorganismG

. 1

@. 2

C. 3

,. 4

Ch22. Organic Compounds, Polymers,And Biochemicals

Documents

Transcript of Ch22. Organic Compounds, Polymers,And Biochemicals