Intro to Organic Chemistry

1
Intro to Organic Chemistry

• Chap 21,22,23

2
Essential Questions

• How do I name straight chain hydrocarbons
• How do I identify functional groups
• What are the important biomolecules
• What special bonds hold polysaccharides/proteins
  together

3
What is Organic Chemistry

• The chemistry of carbon and the compounds it
  forms
• This does not include the carbon oxides (CO,
  CO2), carbonate, etc

4
What is special about the number of bonds and the
kinds of compounds Carbon forms

• Carbon forms 4 covalent bonds. It can bond to
  itself over and over and still to other atoms
  (concatentation)

5
What is a hydrocarbon

• A compound containing only C and H

6
What is a structural formula

• A formula representing each bond in the compound
• CH3CH2CH3

7
How do you draw an (expanded) structural formula
for an organic compound

• Use bonding rules and show with dashes the bonds
  between the atoms

8
Show me propane

• H
  H H H-
  C---------C------C--H
  H H H

9
Organic Nomenclature

• Organic compounds (those that have Carbon as the
  main element) have a special set of rules for
  naming.
• You will need to be able to name some simple
  straight chain hydrocarbons
• The system is based upon the carbon chain in the
  compound

10
What are the root names for the first 10 Carbons

• 1. CH3- meth
• 2. CH3CH2- eth
• 3. CH3CH2CH2 prop
• 4. CH3CH2CH2CH2 but
• 5. CH3CH2CH2CH2CH2- pent
• 6. CH3CH2CH2CH2CH2CH2- hex
• 7. CH3CH2CH2CH2CH2CH2CH2- hept
• 8. CH3CH2CH2CH2CH2CH2CH2CH2- oct
• 9. CH3CH2CH2CH2CH2CH2CH2CH2CH2 - non
• 10.CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2-
  
  dec

11
What suffix do we need for the hydrocarbons

• All C-C single bonds ane (alkane)

12
How do you name a hydrocarbon

• Find longest continuous chain of Cs (may have to
  look up or down. Not always in a straight line).
  This is the root (stem) see above.
• If all single bonds use suffix ane.

13
Give an example

• CH3CH2CH3
• Propane
• CH3CH2CH2CH2CH2CH3
• hexane

14
What is an isomer

• Substances that has the same number and kind of
  atoms but are bonded differently (have different
  structures)
• There are structural, functional, optical, etc,
  isomers

15
Draw some isomers of hexane

• CH3CH2CH2CH2CH2CH3
• CH3
  
  CH3CHCH2CH2CH3
• CH3 CH3 CH3
  CH3CHCHCH3
  CH3CH2CHCH2CH3
• This is one of the reasons there are so many
  different organic molecules

16
What is a functional group

• A specialized group that gives the carbon
  compound special chemical properties.

17
How would you recognize an alcohol

• An -OH group attached to a Carbon Chain

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An example?

• OH CH3CHCH2CH2CH3
• 2-pentanol (drop the e off pentane and add ol)

19
How would you recognize an acid

• COOH,
• COOH
• This will always be at the end of the carbon
  chain

20
How would you recognize an ester

• R-CO O-RR stands for a carbon or a
  bunch of carbons so we look for a C with two Os
  attached and one of the Os has some more Carbons
  attached to it

21
How do you make an ester

• R-CO ROH ? R-CO H2O
  OH O-R
• acid alcohol ? ester water
• This is a dehydration synthesis rxn.
• This is also called a condensation rxn. (two
  things become one thing)

22
How do you make an ester

• CH3CH2CO CH3OH ? CH3CH2CO
• OH OCH
• propanoic acid methyl alcohol ?methyl
  propanoate

23
How would you recognize a ketone

• R-C-R O
• You will see the C to O double bond in the middle
  of the Carbon chain

24
How would you recognize an aldehyde

• R-C-H O
• You will see the C to O double bond at the end of
  the Carbon chain

25
How would you recognize an ether

• R-C-O-R
• You will see the C to O bond in the middle of the
  Carbon chain and the O will bond to more carbons

26
How would you recognize an amine

• R-C-NH2
• The amine group can be at the end or in the
  middle. Just make sure you look for the N

27
How would you recognize an amide

• R-C-NH2 O
• The amide group is at the end of the chain.. It
  is half acid and half amine. Look for the C,O,N

28
How would you recognize a substituted hydrocarbon

• You will see a carbon chain with another element
  (group VII usually) attached to a carbon and
  replacing one of the hydrogens
• CH3 Br Cl
  CH3CHCHCH3
  CH3CH2CHCH2CH3

29
How would you recognize an unsaturated hydrocarbon

• You will see a carbon chain with fewer hydrogens
  than the 4 bonds carbon needs to form
• CHCCH2CH3 Here we see the first C with 1 H and
  that leaves 3 bonds left to form. The 2nd C has
  no Hs on it. It too has to bond 4 times. Since
  it is bonded to 2 Cs that leaves 2 bonds left.
  Usually that is to 2 Hs. since there are no Hs
  here those bonds have to be between it and the
  1st C. This is called a triple bond.

30
How would you recognize an unsaturated hydrocarbon

• CH3CH2CHCHCH3
• Here we see the first C with 3 H and that leaves
  1 bonds left to form to the next C. The 2nd C has
  2 Hs on it and leaves one to each C it is
  attached to. The 3rd C has only 1H.It too has to
  bond 4 times. Since it is bonded to 2 Cs that
  leaves 1 bond left. The next C has the same
  setup. since both are one bond short there will
  be a double bond here.

31
How would you recognize an unsaturated hydrocarbon

• Here is the easy way.
• CH3CH2CHCHCH3
• double lines means 2 bonds
• CH?CH2CH3
• 3 lines means a triple bond
• No lines or one line means a single bond

32
Some Practical Info on Hydrocarbons

• Crude oil is a mixture of many hydrocarbons. We
  know these are nonpolar and only have dispersion
  forces. This makes them relatively low boiling
  pts. The difference in attractions and therefore
  b.p. is the size.
• A fractionating (distillation) tower starts out
  with high temp at the bottom and gets cooler in
  stages as it rises. The larger molecules will
  condense first (higher temps) and leave the
  lighter ones to climb the tower. They will
  continue to separate
• See p.747

33
Some Practical Info on Hydrocarbons

• 100o etc
• 200o etc
• 300o subs that boil above 300
  will condense out those that have
  lower will continue to rise
• 400o subs that boil above 400
  will condense out those that have
  lower will continue to rise

34
What are some biologically important organic
compounds

• Proteins,
• carbohydrates,
• lipids (fats)

35
How would you recognize a carbohydrate

• A poly hydroxy aldehyde or ketone

36
Some info on carbos Mono, di. Poly sac

• Monosaccharide one carbo(sugar) molecule
• Disaccharide two monos bonded together
• Poly many (12 or more)

37
Glycosidic bonds

• A bond between an oxygen in the alcohol group on
  one carbo and the oxygen in an alcohol bonded to
  an acetal carbon

38
How would you recognize a lipid

• Cmpd containing C,H,O and is insoluble in water.
• (It is an ester with the R group on the acid
  portion being a fatty acid. (even number of Cs)
• R-CO O-RThey are commonly
  called fats or oils (fat solid, oil
  liquid)(see triglycerides)

39
Fatty acid

• Long chain organic acid with an even number of
  Cs (natural 12-24)

Saturated vs unsaturated
Like the afore mentioned hydrocarbons.
Unsaturated have double or triple bonds in them.
(remember the phrase contains polyunsaturated
40
Triglycerides

• 3 fatty acids bonded to glycerol (3 carbon
  molecule with 3 alcohol groups)
• Body stores excess energy (fat) in these
  triglycerides.

41
Wax

• Glycerol with long chain fatty acids. (candles,
  carnuba for waxing cars)

42
Steroids

• Lipids that use a typical 4 fused ring base.
• (Sex hormones, anabolic steroids, cholesterol)

43
How would you recognize a protein

• A complex molecule consisting of a particular
  sequence of amino acids (peptides) that are
  joined to form a protein (polypeptides). All
  proteins consist of carbon, hydrogen, oxygen and
  nitrogen Series of amino acids (acid group and
  amine group on same molecule)bonded together to
  form amides.

44
Amino acids

• Organic molecules with both an amine and acid
  (carboxyl)functional groupsMay contain a side
  Chain (R group)

45
Peptide

• A Chain of two or more amino acids linked by a
  peptide bond

46
Peptide bond

• A Bond formed when the hydroxyl (OH) group of one
  amino acid combines with the H of the amine group
  of another amino acid

47
Polypeptide vs protein

• Protein has usually 50 or more amino acids in the
  chain
• Enzymes, support (tendon, ligament), insulin are
  all proteins

48
Nucleic Acids

• A nitrogen containing biological molecule
  involved in storage and transmission of genetic
  information.
• Monomer is a nucleotide phosphate, 5 C sugar,
  nitrogen base.

49
DNA