Chemistry 2100
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Chemistry 2100. Fall 2011. Bloom’s Taxonomy. Richard C. Overbaugh, Lynn Schultz Old Dominion University. Student Objectives for this course. Analyze and explain chemical differences among the various classes of organic compounds Evaluate carbohydrate structure and reactivity

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Chemistry 2100

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Chemistry 2100

Fall 2011


Bloom’s Taxonomy

Richard C. Overbaugh, Lynn SchultzOld Dominion University


Student Objectives for this course

  • Analyze and explain chemical differences among the various classes of organic compounds

  • Evaluate carbohydrate structure and reactivity

  • Compare and contrast the four main classes of key biomolecules

  • Explain the processes of protein folding and enzymatic catalysis

  • Use knowledge of replication, transcription, and translation to predict the outcome of genetic diseases

  • Relate biochemical concepts to digestion, metabolism, and nutrition


Organic & Biological Chemistry


General Chemistry

element covalent bonds lone pairs

H 1 0

C 4 0

N 3 1

O 2 2

X 1 3

~109.5°


Valence Shell Electron Pair Repulsion Theory

regions of predicted predicted

electron density geometry bond angles

4tetrahedral 109.5°

3 trigonal planar 120°

2 linear 180°

120°

~109.5°

180°

120°


Meet the Elements

http://www.youtube.com/watch?v=Uy0m7jnyv6U


English Language

Shorthand

Cursive

Type

Print


The language of Chemistry

3D Structural Formula

Molecular Formula

C2H6O

Structural Formula

Skeletal, line-angle Formula

Condensed

Structural Formula

Molecular Representation

CH3CH2OH

or


Alkanes

  • Simplest hydrocarbons

  • Composed of only single bonds

  • Often referred to as aliphatic hydrocarbons

    • From Greek aleiphar (fat or oil)

  • Also called Paraffins

    • From Latin parum affinis (barely reactive)

  • General formula: CnH2n+2


Methane & Ethane


Propane & Butane


Butane & Constitutional Isomers

C4H10

n-butane

isobutane


How many constitutional isomers?

constitutional (structural) isomers

C20H42 366,319

C30H62> 4 billion

C40H82> 65 trillion

C20H42 366,319

C30H62 > 4 billion

C40H82> 65 trillion

C5H123

C6H145

C10H2275


Naming Conventions: IUPAC Nomenclature

  • International Union of Pure and Applied Chemistry

  • Gives a set of unambiguous names

  • Despite this, common names are still used


Naming Alkanes

#C Prefix + -ane

C1 "meth" Gr., methy (wine)*

C2 "eth" Gr., aithein (blaze)

C3"prop" Gr., protos pion (first fat)*

C4"but" L., butyrum (butter)

C5"pent" Gr., pente (five)

C6"hex" Gr., hex (six)

C7"hept" Gr., hepta (seven)

C8"oct" L., octo (eight)

C9"non" L., nona (nine)

C10"dec" L., deca (ten)


Alkyl groups


Naming Algorithm

Parent

Substituents—

—Suffix

IUPAC Rules

(a) parent C-chain

(b) substituents

(c) numbers

(d) alphabetical listing


Dreadful Details!

  • 1. The name for an alkane with an unbranched chain of carbon atoms consists of a prefix showing the number of carbon atoms and the ending -ane.

  • 2. For branched-chain alkanes, the longest chain of carbon atoms is the parent chain and its name is the root name.

  • 3. Name and number each substituent on the parent chain and use a hyphen to connect the number to the name.

  • 4. If there is one substituent, number the parent chain from the end that gives the substituent the lower number.


Dreadful details (part 2)!

  • 5. If the same substituent occurs more than once:

    • Number the parent chain from the end that gives the lower number to the substituent encountered first.

    • Indicate the number of times the substituent occurs by a prefix di-, tri-, tetra-, penta-, hexa-, and so forth.

    • Use a comma to separate position numbers.

  • 6. If there are two or more different substituents

    • List them in alphabetical order.

    • Number the chain from the end that gives the lower number to the substituent encountered first.

    • If there are different substituents at equivalent positions on opposite ends of the parent chain, give the substituent of lower alphabetical order the lower number.

  • 7. Do not include the prefixes di-, tri-, tetra-, and so forth or the hyphenated prefixes sec- and tert- in alphabetizing;

    • Alphabetize the names of substituents first, and then insert these prefixes.


Alkane Origins


Physical Properties of Alkanes


Isomers and Physical Properties

pentane

bp 36°C; mp -130°C

d 0.626

neopentane

bp 9°C; mp -16°C

d 0.606

isopentane

bp 28°C; mp -160°C

d 0.620


Alkane Origins


C6-C12 mixture

Gasoline, Combustion, & Octane Ratings

CH4 + 2O2 CO2 + 2H2O + 212 kcal/mol

CH3CH2CH3 + 5 O2 3 CO2 + 4H2O + 530 kcal/mol

but…

2 CH3CH2CH3 + 7 O2 2 CO2 + 2 CO + 2 C + 8H2O + < 530 kcal/mol

Octane Rating – Controlled Explosions

Ethanol

Octane rating 105

2,2,4-trimethylpentane

(iso-octane)

Octane rating 100

Heptane

Octane rating 0

Octane

Octane Rating -20


Halogenation

dichlorodiphenyltrichloroethane

DDT

polytetrafluoroethylene (PTFE)

Teflon

dichlorodifluoromethane

Freon

Perfluorodecalin


60° 90° 108° 120° 128° 135°

Cycloalkanes

CnH2n

60° 88° 105° 109° 109° 109°


Cholesterol

Muskone

Interesting Cycloalkane Derivatives

Testosterone

Estradiol


Cyclohexane


Cyclohexane – the Chair

6

1

5

4

2

"chair"

3


CH3

CH3

H

H

H

H

H

H

(1)

(1)

H

H

4

4

1

1

H

H

2

2

(3)

(3)

(3)

(3)

3

3

2

2

3

3

6

6

(3')

(3')

(3')

(3')

5

5

6

6

5

5

(1)

(1)

CH3

CH3

1

1

4

4

95% 5%

1,3-diaxial interactions

H

H

Cyclohexane Substituents


H

H

Cl

H

Cl

H

Cl

H

H

Cl

H

H

Cl

Cl

Cl

Cl

Haworth

perspective

Haworth

perspective

cis-1,2-dichlorocyclopentane

trans-1,2-dichlorocyclopentane

Geometric Isomers, a.k.a.cis-trans isomers


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