Organic Chemistry A. Carbon Compounds

Organic Chemistry A. Carbon Compounds
organic compounds are those in which carbon atoms are almost always bonded to each other, to hydrogen atoms and a few other atoms (O, N, S, P) inorganic exceptions are the oxides of carbon, carbonates, cyanides and carbides (no C-C bonds or C-H bonds) eg) CO2, CaCO3, NaCN, SiC there are millions of organic compounds and all contain covalent bonds

carbon is unique for two reasons:
it can bond with atoms to form long chains, rings, spheres, tubes, sheets etc. other carbon b) it can form combinations of single, double and triple bonds (no other element does this!!!!)

recall polarity and intermolecular forces from the chemical bonding unit
polar bonds are formed when there is an uneven pull on e polar compounds are formed when the polar bonds within a molecule do not cancel each other out the presence of dipole-dipole forces and hydrogen bonding will allow polar compounds to dissolve in water, since it is also polar non-polar compounds only have LD forces between molecules and will not dissolve in water

B. Structural Isomers isomers are compounds with
the same molecular formula but a different structure

Draw the three structural isomers for C5H12.
Example 1 Draw the three structural isomers for C5H12. 1. 2. H C H CH3 C 3. H C H3 C CH3

Draw three structural isomers for C4H8F2 .
Example 2 Draw three structural isomers for C4H8F2 . 1. 2. H F C H F C 3. H F C

different structures result in different
properties the arrangement of the atoms determines the types of intermolecular attractions which then determines properties such as and in water boiling point solubility

Example Draw two isomers of C3H8O. Which one would have a boiling point of 7.4C and which would have a boiling point of 82.5C? Explain why the boiling points are so different. H C OH H C O has HB between molecules which makes the boiling point quite high 82.5C – does not have HB between molecules therefore the boiling point is significantly lower 7.4C –

C. Formulas and Structural Diagrams
organic molecules can be drawn in three different ways: 1. complete structural diagram – shows all bonds eg) C3H8 H C eg) C3H7F H C F

2. condensed structural diagrams – shows. but includes the etc
2. condensed structural diagrams – shows but includes the etc. attached to each carbon carbon to carbon bonds hydrogens eg) C3H8 CH3 CH2 eg) C3H7F CH3 CH2 CH2F

3. line structural diagrams – shows only bonds
carbon to carbon eg) C3H8 eg) C5H12 eg) C4H8

1. Number of Functional Groups
D. Prefixes 1. Number of Functional Groups 6 = 2 = = 3 = = 4 = = 5 = = hexa di hepta tri octa tetra nona penta deca

2. Number of Carbons 1 = 6 = 2 = 7 = 3 = 8 = 4 = 9 = 5 = 10 = meth hex
1 = = 2 = = 3 = = 4 = = 5 = = meth hex eth hept prop oct but non pent dec

E. Alkanes CnH2n+2 eg) C5H12, C20H42, etc. hydrocarbons containing
only single bonds ie) they are SATURATED can be continuous chains, chains, structures long branched ring (cycloalkanes)

1. Properties nonpolar not soluble in water can be depending on number of carbon atoms solid, liquid or gas relatively because the bonds are unreactive single very stable

2. Uses natural gas, BBQ’s, lighter fluid, gasoline etc good for making plastics, lubricants 3. Naming IUPAC = International Union of Pure and Applied Chemistry

prefix + “ANE” (suffix)
i. Continuous Chains prefix + “ANE” (suffix) eg) H C butane

ii. Branched Chains branches are called functional group alkyl 1 C = ; 2C = ; 3 C = etc methyl ethyl propyl find the and so the branches get the longest carbon chain number it lowest possible numbers to name: name the first (in order), including the where each group is found, then name the groups alphabetical number of the carbon longest chain (parent name)

eg) 3-methylpentane methyl 3-ethyl-2-methylpentane methyl ethyl H CH3
1 2 3 4 5 methyl H CH2 C CH3 1 2 3 4 5 3-ethyl-2-methylpentane methyl ethyl

eg) H CH3 C 5 4 3 2 1 methyl methyl 2,3-dimethylpentane

iii. Cycloalkanes use the as the name ring structure “parent” + +
“cyclo” prefix ANE eg) cyclobutane cyclopropane

lowest possible number sequence
if there are branches, number the carbons in the ring so the branches get the lowest possible number sequence eg) CH3 CH2 5 4 1 ethyl 3 2 methyl 1-ethyl-3-methylcyclopentane

F. Alkenes CnH2n eg) C5H10, C20H40, etc. hydrocarbons containing
one or more double bonds ie) they are UNSATURATED can be continuous chains, chains, structures long branched ring (cycloalkenes)

1. Properties nonpolar not soluble in water than corresponding alkane because they have which makes the forces of attraction lower boiling point fewer e LD weaker eg) ethane BP = 88.6C ethene BP = 103.8C than alkanes more reactive double bond has in the same area  and more e- greater repulsion bond less stable

***alkenes with these substances causing a noticeable alkanes will not
diagnostic test: use KMnO4(aq) or Br2(l) ***alkenes with these substances causing a noticeable alkanes will not (double bond) will react colour change, A B Br2(l) KMnO4(l) alkene alkane alkane alkene *** the alkenes will react causing the colour to disappear as the coloured substance is used up in the reaction

2. Uses plastics (PVC) steroids welding torches 3. Naming i. Continuous Chains prefix + “ENE” (suffix) number carbons to give the the double bond lowest number the number where the double bond is to be given as a “ # ” between the prefix and the suffix starts

H C ‗ eg) hex-3-ene H C ‗ pent-2-ene H C ‗ but-1-ene

ii. Branched Chains find the longest carbon chain and number it so the gets the double bond lowest possible number to name: name the first (in order), including the of the carbon where each is found, then the including the of the carbon where the double bond starts groups alphabetical number parent name number

eg) 2-ethylhept-1-ene 4,5,6-trimethylnon-2-ene CH2 C ‗ CH3 CH CH3 CH2

iii. Cycloalkenes double bond is always numbered 1, 2 get the after the branches lowest numbering sequence double bond “cyclo” prefix ENE list branches in with the alphabetical order number of the carbon they are on

eg) cyclohexene cyclopropene 3-ethylcyclobutene
CH2 CH3 2 3 3-ethylcyclobutene 1 4 CH2 CH3 4 1 2 3 3-ethyl-1,3-dimethylcyclobutene

G. Alkynes CnH2n-2 eg) C5H8, C20H38, etc. hydrocarbons containing
one or more triple bonds ie) they are also UNSATURATED can be continuous chains, chains long branched not plentiful in nature

1. Properties nonpolar very reactive (more than alkanes and alkenes) bond has in the same area  force of repulsion triple 6 e- high boiling points are than corresponding alkanes and alkenes because of their and the of triple bonds higher linear structure nature 2. Uses welding torches

3. Naming i. Continuous Chains prefix + “YNE” number carbons to give the the triple bond lowest number the number where the triple bond is to be given as a “ # ” between the prefix and the suffix starts

eg) C H ≡ hex-3-yne C H ≡ pent-2-yne

ii. Branched Chains find the and number it so the gets the lowest number longest carbon chain triple bond to name: name the first (in order), including the of the carbon where each is found, then the including the of the carbon where the triple bond starts groups alphabetical number parent name number

eg) 3-propyloct-1-yne 2,5,6-trimethyloct-3-yne CH2 CH C ≡ CH3 C CH3 CH

Review alkanes – branches, rings – least reactive alkenes – branches, rings alkynes – branches – most reactive all called aliphatics all and in water nonpolar not soluble major intermolecular forces are boiling points are LD low

H. Aromatics hydrocarbons containing one or more benzene rings C6H6 OR all bonds are the same length and strength we draw benzene like this:

1. Properties nonpolar the benzene ring structure is very stable aromatics are characterized by strong aromas

2. Uses ASA, amphetamines, adrenaline, benzocaine (anesthetic) moth balls, TNT wintergreen, menthol, vanilla, cinnamon SPF in sunscreen

3. Naming i. Benzene as a Branch
if you have a really long carbon chain, it is easier to call the benzene ring a “phenyl” group CH3 CH2 CH eg) 4-phenylheptane CH2 CH C ‗ CH3 3-methyl-5,5-diphenyloct-1-ene

ii. Benzene as a the Main Compound
if only one group is attached, give the attached to alkyl name “benzene” (no number is necessary) eg) CH3 methylbenzene

if there is more than one branch, number them so they get the and name
lowest sequence alphabetically CH3 CH2 eg) 1-ethyl-3-methylbenzene CH3 CH2 1,3-dimethyl-5-propylbenzene

CH3 C2H5 1-ethyl-3-methylcyclohexane ***Watch out for this!!!

R - OH I. Alcohols organic compounds with one or more OH (hydroxyl) groups 1. Properties have much than corresponding aliphatics because of higher boiling points hydrogen bonding! eg) methane (CH4) BP = methanol (CH3OH) BP = -162C 65C

polar the end of the alcohol is while the end  small alcohols are in water and large alcohols are –OH polar carbon chain is not soluble not 2. Uses antifreeze, rubbing alcohol, beverages, moistening agent

3. Naming number the longest carbon chain containing the so the group gets the hydroxyl group –OH lowest number name at end aliphatic (without “e” ) + “OL” give the where the is found between the parent name and the suffix number for the carbon –OH group

if there is hydroxyl group, use a prefix ( ) to indicate the of OH groups and place the numbers between the parent name and the suffix more than one di, tri, tetra number ***Note, if the suffix starts with a vowel, drop the “e” on the parent name; if the suffix starts with a consonant, keep the “e” on the parent name

H OH C eg) butan-2-ol H OH C CH3 3-methylbutan-2-ol

H OH C CH3 2-methylbutane-2,3-diol an unusual case: OH phenol

J. Organic Halides R - X where is and is a R carbon chain or ring X halogen organic compounds where has been replaced by hydrogen one or more halogens (F, Cl, Br, I) do not readily occur in nature

1. Properties can be or , depending on the placement of the halogen groups polar nonpolar many are toxic and dangerous 2. Uses manufactured for human use eg) DDT, PCB, CFC anesthetics dry cleaning fluid plastics, polymers (Teflon)

same rules as before… name branches ( included now) halogens
3. Naming same rules as before… name branches ( included now) halogens alphabetically F = fluoro Cl = chloro Br = bromo I = iodo eg) Cl H C 2,3-dichlorobutane

2-fluoro-4-iodo-1-methylbenzene
CH3 I 2-fluoro-4-iodo-1-methylbenzene

organic compounds containing the carboxyl functional group (-COOH)
║ O R C K. Carboxylic Acids where is R carbon chain or ring organic compounds containing the carboxyl functional group (-COOH) 1. Properties polar  dissolve in water boiling points due to high hydrogen bonding weakly acidic diagnostic test: use (will turn ), litmus paper red readily react with metals, neutralize bases

2. Uses recycling rubber – methanoic acid vinegar – ethanoic (acetic) acid rust remover – oxalic acid fruits – citric acid 3. Naming count the longest carbon chain including the carbon in the carboxyl group the carbon in the carboxyl group is always number 1 drop and add “e” “OIC ACID”

eg) OH ║ O C H methanoic acid OH ║ O C H ethanoic acid

OH ║ O C benzoic acid O H H H ║ I C C C C OH H H H 4-iodobutanoic acid

where can be a carbon chain or hydrogen and can be a carbon chain R R’
║ R C R’ L. Esters where can be a carbon chain or hydrogen and can be a carbon chain R R’ combination of a and an carboxylic acid alcohol 1. Properties polar esters in water, esters small dissolve large do not boiling points slightly lower than corresponding carboxylic acids and alcohols due to lack of hydrogen bonding

very which allows them to generate
volatile aromas 2. Uses flavouring agents 3. Naming identify the used to make the ester alcohol change the alcohol name to the corresponding name alkyl eg) methanol would become methyl identify the the ester was made from carboxylic acid

drop the “oic acid” and replace with
“oate” eg) butanoic acid would become “butanoate” put the together with a in between two names space eg) methyl butanoate you can have on esters…they follow the alphabetical rule, numbering begins at the of the alcohol and the C=O end of the carboxylic acid branches O end

eg) O ║ C H ethyl butanoate O ║ C H CH3 propyl propanoate

ethyl 2-methylbutanoate
eg) O ║ C H CH3 ethyl 2-methylbutanoate

M. Boiling Points and Solubility
we can compare the boiling points of various organic compounds using their and the between the molecules polarity intermolecular attractions Example 1 Put the following organic compounds in order from highest boiling point to lowest boiling point. alcohol, alkane, alkene, aromatic, carboxylic acid carboxylic acid alcohol aromatic alkane alkene highest lowest

Example 2 Put the following homologous series of organic compounds in order from highest boiling point to lowest boiling point. C2H6, C2H5OH, CH3COOH, C2H4 CH3COOH C2H5OH C2H6 C2H4 highest lowest

we can also compare the of various organic compounds using their polarity
solubility Insoluble Organic Compounds Soluble Organic Compounds aliphatics – alkanes, alkenes, alkynes carboxylic acids aromatics alcohols – large (7 or more carbons) alcohols – small (less than 7 carbons) esters – large esters – small organic halides organic halides

N. Organic Reactions 1. Combustion Reactions occurs when a reacts with hydrocarbon oxygen products are always carbon dioxide and water these are economically important reactions for they are the major reactions that produce required for fuelling our vehicles, heating our homes, and producing electricity thermal energy eg) C5H12(l) O2(g)  1 8 5 CO2(g) 6 H2O(g)

1 C5H12(l) + 8 O2(g)  5 CO2(g) + 6 H2O(g)
eg) 1 C5H12(l) O2(g)  5 CO2(g) H2O(g) H C O2(g)  4 CO2(g) H2O(g) ***balance these reactions

2. Addition Reactions a or bond in an alkene or alkyne is and a group or element is (a catalyst is present) double triple broken added eg) H C ‗ Cl +  Cl H C

H C ‗ OH +  H OH C H C ‗ +  H C

H C ‗ Br +  H Br C H C Cl ‗ C H ≡ 1 Cl2 +  Cl H C C H ≡ 2 Cl2 + 

3. Substitution Reactions
the replacement ( ) of a hydrogen on an alkane or aromatic with (eg. F, Cl etc) substitution another atom commonly used to make organic halides Examples C H 1. C H Cl cat H - Cl + + Cl – Cl 

Br 2. Br – Br +  cat H - Br + 3.  cat I + I – I H - I + 4. H C H Br C Br2 +  cat H - Br +

4. Esterification Reactions the reaction of a with an carboxylic acid
alcohol the catalyst is sulphuric acid Examples 1. OH ║ O C H HO +  H2SO4(aq) O ║ C H + H – OH

2.  H2SO4(aq) OH ║ O C H + HO + H – OH C H O ║

5. Elimination Reactions an has water removed, forming an plus the
alcohol alkene water can react with a to produce an , a and organic halides base (hydroxide) alkene halide ion water Examples 1. H OH C H C ‗ +  cat H – OH

2. 3. ‗ H C OH H C ‗ +  cat H – OH H Cl C H C +  cat + OH  H – OH

6. Polymerization Reactions
a is a that forms the for a polymer monomer simple molecule base unit a is a formed by the of polymer very, very long molecule bazillions of monomers covalent bonding depending on the polymer, the monomers that make it up can be or the same different

polymers can be natural eg) carbohydrates, proteins, DNA

polymers can be synthetic eg) nylon, PVC, Teflon, polyester

polymers that can be heated and molded into specific shapes are commonly called
plastics plastics are one type of synthetic compound that has been of great benefit to society (although there are also problems associated with then) the names of polymers are the monomer name with in front “poly” many have classical names instead of IUPAC names

the polymer is the formed only product
Addition Polymers formed when the electrons in double or triple bonds in the monomer units are rearranged the polymer is the formed only product Examples 1. H C ‗ +  cat H C n … … polyethene

polyvinyl chloride (PVC)
2. F C ‗ +  cat F C n … Teflon 3. H Cl C ‗ +  cat H Cl C n … polyvinyl chloride (PVC) 4. H C n … H C ‗ +  cat polystyrene (styrofoam)

Condensation Polymers
polymerization reactions that involve the formation of a (commonly ) as well as the small molecule water polymer each monomer must have functional groups two two common linkages formed: linkage – between carboxyl group (COOH) and hydroxyl group (OH) ester linkage – between amino group (NH2) and carboxyl group (COOH) amide

Examples 1. C  OH O HO ║ H + n ∙∙∙ C O ║ H + H2O ester linkage
cat OH O HO ║ H + n ∙∙∙ C O ║ H + H2O ester linkage polyethylene terephthalate PET

2. C H O HO N ║ + cat  amide linkage n ∙∙∙ + H2O C O H N ║ protein

O. Petroleum Refining Alberta has vast reserves of petroleum in the form of natural gas, crude oil and oil sand deposits most of this petroleum is refined and then burned as fuel petrochemicals are also used in the production of plastics

is used to separate the components fractional distillation
refining of petroleum separates the crude mixture into purified components is used to separate the components fractional distillation distillation works because of the different of the components of crude oil boiling points the the molecule and the the boiling point, the it rises in the tower (asphalt, fuel oil, wax at bottom; gasoline at top) lighter lower higher distillation tower:

two types of reactions in petroleum refining:
1. Cracking long chain hydrocarbons into breaks smaller units cracking requires heat and pressure there are many different types of cracking reactions, forming different products (alkanes, alkenes) eg) catalytic cracking, steam cracking, hydrocracking hydrocracking requires H2(g)

Examples 1. C17H36 +  C9H20 + H2(g) C H 2.  cat 8 18 cat + H2(g) CH3

small hydrocarbons are to make joined larger molecules
2. Reforming small hydrocarbons are to make joined larger molecules requires heat and pressure there are several types of reforming reactions eg) alkylation to produce “high octane” gasoline all reforming reactions produce H2(g) Example C7H C12H  C H H2 19 40

Examples 1. C7H16 + C12H26  + C H H2 2. ethane + octane
19 40 2. ethane octane decane + hydrogen gas

Organic Chemistry A. Carbon Compounds

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