organic polymer biochemicals

8/12/2019 Organic Polymer Biochemicals

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Organic Compounds, Polymers,and

Biochemicals


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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. Amines are organic derivatives of ammonia

22.5. Organic compounds with carbonyl groups includealdehydes, ketones, and carboxylic acids

22.6. Polymers are composed of many repeating molecularunits

22.7. Most biochemicals are organic compounds22.8. Nucleic acids carry our genetic information

Index


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Organic chemistry is the study of carbon compounds 3

Organic Compounds Are Diverse

Carbon compounds are greatly variant due to theproperties of C:

C is able to bond multiply

C is able to bond with a wide variety of elements

Isomers are possible when there is a carbon chain

Combinations of functional groups give great diversity

Carbon can form rings


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Carbon Compounds

Carbon containing compounds exist in largevariety, mostly due to the multiple ways in which

C can form bonds

Some groups of atoms with similar bonding are

commonly seen, called functional groups.

Molecules may contain more than one functional

group

Can form chiral compounds


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VSEPR (Valence Shell Electron Pair

Repulsion)Structures

HC

CC

CC

H

H H H

HH

H H H

HH

a model in chemistry used to predict the shape of individual

molecules based upon the extent of electron-pair electrostatic

repulsion

Show all atoms Show attachments between atoms but not how many pairs of

electrons were used

Show the geometric arrangement of the atoms


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Condensed Structures

CH3CH2CH2CH2CH3

show the general arrangement of the atoms and thenumber of atoms

no effort is made to indicate geometry, types of bonds,

or lone pairs


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Alcohols & Ethers

Contain C, H, and O, all with single bonds. Alcohols end inOH (R-OH)

Ethers have an O atom in the chain (R-O-R)


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The Carbonyl Group

When C in a chain has a double bond to an oxygen, thegroup is termed a carbonyl

Aldehydes, ketones and carboxylic acids all contain

carbonyl groups

acidcarboxylicketonealdehydeO'

||||||

H

O

CRR

O

CRH

O

CR


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Aldehydes & Ketones

Each has a carbon chain terminating in a carbonyl. Aldehydes then have an added H (RCOH)

Ketones have another carbon chain (RCOR)


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Amines & Amides

Amines contain -NH2on carbon chain (RCNHR) Amides contain NH2on carbon chain with

carbonyl (RCONH2)


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Carboxylic Acids & Esters

Both have a carbon chain terminating in acarbonyl

Carboxylic acidsthen have anOH group

A combined carbonyl and hydroxyl group form a

carboxylgroup (RCOOH)

Estersthen have a singly bound O, then another

carbon chain (RCOOR)


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Functional Groups And Their Properties

Polar functional groups contain O and N Like dissolves like: polar solvents will dissolve

the polar functional groups


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Your Turn!

Which of the followingcontains an amide

group?

A. The top structure

B. The middle

structure

C. The bottom

structureD. None of these


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Hydrocarbons consist of only C and H atoms 14

Lewis Structures Of Hydrocarbons

H C C C C C H

H

H

H

H

H

H

H

H

H

H

Show all atoms, and all electrons Bond pairs usually shown as a line

Non-bonding (lone) pairs of electrons are shown

as dots


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Stick Figures

Each vertex and terminus is a carbon

Assumes that the termini contain as many H as

needed for saturation of the C

All hetero-atoms are shown explicitly

Double bonds explicitly shown

HC

CC

CC

H

H H H

HH

H H H

HH

CC

CC

C


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Your Turn!

Which is the correct formula for the structureshown?

A. C42H12

B. C24

H12

C. C36H12

D. None of these


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Alkanes & Alkenes

Alkanes are hydrocarbons (contain only C and H) have a ratio of atoms CnH2n+2

Alkenes- hydrocarbons with fewer H than the

alkanes (CnH2n)

Use the same prefixes, but have the suffix -ene.


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Alkanes (CnH2n+2)

Composed of hydrocarbon chains in which carbonsare attached to one another by single bonds

Are named by the number of C in the chain and

where any substitutions are found

Prefixes and the associated numbers of carbon

atoms

meth-1 hex-6

eth-2 hept-7

prop-3 oct-8

but-4 non-9

pent-5 dec-10


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Naming Alkanes

1. Find the longest continuous chain of carbons-the root.2. a. Name the root by adding -ane to the appropriate

prefix (a 4-carbon chain would be butane)

b. Identify any branches, and name each by the

number of carbons (a 1-carbon branch is methyl-)3. a. List side chains in alphabetical order, before theroot

b. Use di, tri, tetra (etc) if you have more than one

of something


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Naming (Cont.)

4. Number root from side closest to the firstbranch

5. Use numbers to tell where the side chains

sprout from the root

6. Use the prefix cyclo for ring systems


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Name the following

4-ethyl-2-methylhexane

3-methylheptane

2,3,3,4-tetramethylhexane


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Your Turn!

Name the structure shown:A. 1,2-dimethylpentane

B. 3-methylhexane

C. 2-ethylpentaneD. None of these


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Reactions Of Alkanes

Alkanes are generally stable at room temperature They burn in air to given carbon dioxide

When heated at high temperature they crack(break into

smaller molecules)

etheneethane

HCHCHCHCH

2HCCH

222

raturehigh tempe

33

2

raturehigh tempe

4


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Hydrocarbons with one or more double bonds are

members of the alkene family

open chain alkenes have the general formula C2H2n

Hydrocarbons with triple bonds are in the alkyne

family open chain alkynes have the general formula, CnH2n2

Unsaturated Hydrocarbons


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Naming Alkenes

The parent chain must include the double bond The parent alkene chain must be numbered from

whichever end gives the first carbon of the double

bond the lowest number

The locations of branches are not a factor in

numbering the chain

Alkyl groups are named and located as before


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Name The Following

ethylene 2,3-dimethyl-1-pentene


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Your Turn!

Which name is not correct?

A.

B.

C.

3-pentene

2-pentene

2-methyl-1-butene


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Geometric Isomers

Cisand transisomers exist when thereis a plane of a double bond or of a

ring structure

cissame

trans-opposite


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Alkenes undergo addition reactionsthat eliminate thepi-bond

CH2=CH2+ HCl(g) Cl- CH2-CH3

Inorganic compounds that undergo addition reactionswith alkenes include: H2O, Cl2, Br2, I2, and H2.

Addition Reactions of Alkenes


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Aromatic Compounds

Contain a benzene(C6H5-) ring

Aromatic compounds undergo substitutionreactionsinstead of addition reactions

example: C6H6 + Cl2C6H5Cl + HCl


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Ethers and alcohols are organic derivatives of water 32

Ethers (ROR)

Are almost as chemically inert as alkanes: theyburn and are split apart when boiled inconcentrated acid

Are named by naming each alkyl group,

alphabetically, and end with ether Learning Check:

CH3OCH3

CH3CH2OCH3

CH3CH2OCH2CH3

dimethyl ether

ethyl methyl ether

diethyl ether


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The name ending for alcohols is ol

The parent chain must include the carbon containing the

OHgroup

Learning Check: Name the following

CH3CH2OH

CH3CH2CH2CH2OH

Alcohols (ROH)

ethanol

butanol


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If the alcohol carbon atom holds at least one H atom, it

can be replaced with bonds to oxygen

OH

O

CCHH

O

CCHOHCHCH

acidcarboxylicaldehydealcohol

OH

O

CRH

O

CROHRCH

||

3

oxidationFurther||

3

oxidation

23

||oxidationFurther||

oxidation

2

Oxidation of Alcohols


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The reverse the addition of water to an alkene,

it is an example of an elimination reaction

OHCHCHCHH

OH

CH

H

CCH 2232||

3

Dehydration Of Alcohols:


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Substitution Reactions Of Alcohols

Under acidic conditions, the -OHgroup can bereplaced by a halogen atom

nebromopropa-1propanol-1OHBrCHCHCHHBr(conc)OHCHCHCH 2223223


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Your Turn!

What type of structure is shownA. Alcohol

B. Ether

C. PeroxideD. aldehyde


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Amines are organic derivatives of ammonia 38

Amines

Are derivatives of ammonia where one or morehydrogens have been replaced with alkyl groups

NH3is ammonia

CH3NH2is methylamine

(CH3)2NH is dimethylamine and (CH3)3N istrimethylamine (bp 3oC).

Amines are bases, and react with strong proton

donors to form ammonium ion

(aq)NHCHCH(aq)H(aq)NHCHCH

(aq)NH(aq)H(aq)NH

323223

43


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Amines are organic derivatives of ammonia 39

Are more soluble in water than amines

OH(aq)NHCHCH(aq)OH(aq)NHCHCH

OH(aq)NH(aq)OH(aq)NH

2223323

234

Protonated Amines


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. Organic compounds with carbonyl groups include aldehydes, ketones, and carboxylic

acids

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The name ending for an aldehyde is

al The parent chain is the longest chain that includes

the aldehyde group

propanalethanalmethanal

||

23

||

3

||

HOCCHCHH

OCCHH

OCH

Aldehydes


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Organic compounds with carbonyl groups include aldehydes, ketones, and carboxylic

acids

41

Ketones

The ending for ketones is one. Theparent chain must include the carbonyl

group

32

||

233

||

3 CHCH

O

CCHCHCH

O

CCH

propanone 3-pentanone


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Organic compounds with carbonyl groups include aldehydes, ketones, and carboxylic

acids

42

Reactions Of Aldehydes & Ketones

Aldehydes and ketones can be hydrogenated togive alcohols

propanol-2CHH

OH

CCHHCH

O

CCH

propanol-1OHCHCHCHHH

O

CCHCH

3

|

323

||

3

2232

||

33


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Organic compounds with carbonyl groups include aldehydes, ketones, and carboxylicacids

43

Carboxylic Acids

The name ending for carboxylic acids is oic acid.the parent chain must include the carbonyl carbon,

which is numbered as position 1

The common names are used for these: formic

acid and acetic acid

acidethanoicacidmethanoic

| |

23

||

OH

O

CCHCHOH

O

CH


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Esters

In esters, the OHof the carboxyl group isreplaced by -OR

Name the alkyl group attached to the O atom

followed by a separate word generated from

the name of the parent acid by changing oicacidto -ate

CHOCH

O

CCHOCH

O

C H 32

||

33

||

methyl methanoate ethyl ethanoate


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Esters can be prepared by heating the parent acid with

an alcohol in the presence of an acid catalyst

ethanoateethylethanolacidethanoic

OHCHOCH

O

CCHCHCHHOCHOH

O

CCHCH

OHOR'OCRHOR'OH

OCR

232

||

23

H

32

||

23

2

||H

||

Preparation Of Esters


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Esters are split apart by the action of base in a reactioncalled saponification

ethanolionethanoate

)()(

ethanoateethyl

)()(

23

||

23

32

||

23

OHCHCHaqNaaqO

O

CCHCH

aqNaOHaqCHOCH

O

CCHCH heat

Reactions of Esters


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Polymers are composed of many repeating molecular units 47

Polymers

Are large molecules with repeating units calledmonomers


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Formation Of Addition Polymers

Initiatorsattack a monomer and make it receptivefor the new bond


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Addition Polymer: Polystyrene

Styrene is treated with an initiatorto form a freeradical

Radical end is free to form a new connection to

another styrene molecule


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Crosslinking

Branches on polymersmake them susceptible

to interaction with other

polymers

Increased crosslinkingleads to increased

strength


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Organic Compounds, Polymers,and

Biochemicals

organic polymer biochemicals

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