Organic Chemistry

1
Organic Chemistry

• Chapter 14

2
Goals

• Recognize the importance of organic compounds
• Compare properties of organic vs. inorganic
  compounds
• Become familiar with methods of indicating
  covalent bonds
• Draw and understand structural formulas,
  including isomers
• See structures in three dimensions
• Name organic compounds

3
Organic Chemistry

• The chemistry of compounds containing C.
• Some will contain N, O, P, H
• How many bonds can each element make?
• Properties
• Water soluble? (Polar or nonpolar?)
• What does this tell you about the bonding?
• Will they be electrolytes?
• Melting point and boiling point low
• Can be very high molecular weight

4
Importance of Organics

• They are everywhere!
• Soaps, fats, food, sugars, your body, gasoline,
  oil.
• Side note-
• There is no chemical difference between a PURE
  substance made in the lab vs. isolated from
  nature
• Vanillin vs. vanilla extract
• Vitamin C from oranges vs. ascorbic acid
• Complex mixtures like human milk vs. baby formula
  are not the same because all the components of
  the natural system have not been identified.
• New concern over synthesized organics not found
  in nature showing up in water supply (birth
  control hormones, antidepressants)

5
Bonding

• Covalent
• Each line means 2 electrons
• Single bond C-C
• Aliphatic, saturated
• Double bond CC
• Triple bond C C

6
Types of Formulas

• Molecular
• Tell us which atoms are present and how many, but
  not how they are connected.
• Structural
• Show the arrangement of atoms
• Condensed structural - just like structural, but
  dont show bonds . CH3CH2CH3
• - Line angle formula
• How many ways can you draw C3H8O?

7
Isomers

• Same molecular formula, different arrangement of
  atoms C7H14O2
• Name your compound. Isomers will have different
  names.

8
Shapes of molecules

• Straight or branched chains - aliphatic
• Rings - aromatic, cyclic, or heterocyclic
• Heterocyclic - ring with atom other than C and H

9
Saturated Hydrocarbons

• Chapter 15

10
Alkanes

• Hydrocarbons - contain only C and H
• General formula CnH(2n2)
• Names all end in -ane

11
Naming Alkanes (or understanding your shampoo
label)

• Pick the longest carbon chain.
• Number it so substituents have lowest number.
  Name substituents before parent chain, in
  alphabetical order (2-methyl)
• Prefix indicates number of C, suffix is -ane.if
  no functional groups attached.
• 1 C Meth- 2 C Eth-
• 3 C Prop- 4 C But-
• 5 C Pent- 6 C Hex -
• 7 C Hept- 8 C Oct-
• Know table 15-1 p. 249

12
Nomenclature continued.

• If there is a ring, add the prefix cyclo- to the
  name of the parent chain.
• For alkyl substituents (single bonded C) not on
  the parent chain, add -yl to their name.
• methyl, ethyl, etc.

13
Reactions of alkanes

• CnH(2n2) O2 -gt CO2 H2O
• Remember to balance the equation!

14
Unsaturated Hydrocarbons

• Chapter 16

15
Types of Hydrocarbons

• Alkanes
• Alkenes - contain a double bond, bio impt.
• cis - big group on same side
• (both above or below bond)
• trans - big group opposite side
• (one above, one below bond)
• Alkynes - contain a triple bond
• Aromatics - benzene rings with multiple double
  bonds.

16
Cis or Trans?
17
Naming unsaturated hydrocarbons

• Same rules as alkanes except
• Suffix is -ene for alkenes, -yne for alkynes
• Number so the double bond will have the lowest
  number, and indicate it in the name.
• Example - 1-butene vs. 2-butene

18
Caution chemistry humor

• Bicyclononene
• Frosty the alkane
• Mickey Mouse

19
Reactions of alkenes

• Skip reactions of alkenes except
• Hydrogenation
• CC H2 ---gt H-C-C-H

20
Functional Groups

• The part of an organic molecule involved in
  chemical reactions, physical properties,
  classification of families, and naming cmpds.
• Alcohol R-OH
• Primary, secondary and tertiary based on number
  of carbons bonded to the C with the OH
• Ether R-O-R
• Amine N with one, two, or three R groups. RNH2,
  R2NH, R3N
• Primary secondary and tertiary

21
More functional groups..

• Aldehyde H-CO
• R
• Ketone R-CO
• R

22
And more

• Carboxylic Acid (organic acid)
• R - CO
• OH
• Ester R-C O
• O- R
• Know structures, not reactions.

23

• What functional groups are on vanillin?