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UNIT 6. Theories of Covalent Bonding and Intro to Organic Chemistry: Nomenclature of Alkenes, Alkynes, Alcohols. Structural Isomers Have the Same Molecular Formula. Draw the line angle structure of:.

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Unit 6

UNIT 6

Theories of Covalent Bonding and Intro to Organic Chemistry: Nomenclature of Alkenes, Alkynes, Alcohols


Unit 6

Structural Isomers Have the Same Molecular Formula

Draw the line angle structure of:

The molecular formula of this compound is C8H18. Draw three more structural isomers of octane.


Unit 6

Valence Bond Descriptions

.. .. ..

:O = S = O:

What orbitals overlap to form each of the bonds in SO2?

  • The S-O sigma bond in each double bond is formed by the overlap of an O sp2 hybrid orbital with a S sp2 hybrid orbital.

  • Each S-O pi bond is formed by the overlap of the S 3pz orbital with the O 2pz orbital.

  • Two sp2orbitals on each of the O’s and one sp2 orbital on the S are not involved in any bond.


Unit 6

Nomenclature of Alkenes

  • Number the C chain from the end that brings you to the double bond sooner, then use the alkane naming rules and -ene.

    IUPAC (common)

    H2C=CH2ethene (ethylene)

    H2C=CH-CH3propene (propylene)

  • Planar geometry around the double bond

  • 120° bond angles to the C atoms in the double bond


Unit 6

Nomenclature of Alkenes

cis-but-2-ene

bp = 4°C

methylpropene

bp = - 7°C

geometric isomers

but-1-ene

bp = -6°C

What are the bond angles?

All four are structural isomers.

trans-but-2-ene

bp = 1°C


Unit 6

Nomenclature of Alkenes

Name this alkene.

6,6-dichloro-5-ethyl-4-methylhept-1-ene

Give a VB description of the C-Cl bond.

Draw the line angle structure for

1-chloro-3-methyl-1,3-butadiene


Unit 6

Alkynes

  • Contain at least one C≡C bond. Alkynes are unsaturated molecules.

  • The two π bonds make the geometry through the triple bond linear.

  • The triple bond is highly reactive, so alkynes are not found widely in nature, though they are used as intermediates in industrial processes.


Unit 6

Nomenclature of Alkynes

  • Number the C chain from the end that brings you to the triple bond sooner, then use the alkane naming rules and -yne.

    IUPAC (common)

    HC≡CHethyne (acetylene)

    HC≡C-CH3propyne

  • Linear geometry around the triple bond

  • 180° bond angles to the C atoms in the triple bond


Unit 6

Alkynes

Draw the condensed structural formula and line angle structure for 4-methylpent-2-yne.

CH3 - C≡ C - CH - CH3

|

CH3

CH3C≡CCH(CH3)2

*

What is the hybridization on the starred C? What is the geometry? Give a VB description of one of the C-C pi bonds.


Unit 6

Alcohols

  • Contain the -OH (hydroxyl) group.

  • Alcohols are NOT bases. In fact, some can be acidic (phenol).

  • Can be soluble in polar solvents such as water (hydrocarbons are not soluble in water).

  • Primary (1°) alcohols: R – CH2 - OH

  • Secondary (2°) alcohols:R - CH - R'

    |

    OH

  • Tertiary (3°) alcohols: R″

    |

    R - C - R'

    |

    OH

R,R',R″ designate the rest of the molecule. R represents an alkyl group.


Unit 6

Nomenclature of Alcohols

Number the C chain from the end that brings us to the -OH group sooner, then use the alkane naming rules and -ol.

1° alcoholsIUPAC (common)

CH3CH2OHethanol (ethyl alcohol)

CH3CH2CH2OHpropan-1-ol (n-propyl alcohol)

or 1-propanol

*CH3OH*Methanol is not primary, it’s a methyl alcohol.


Unit 6

Nomenclature of Alcohols

Number the C chain from the end that brings us to the -OH group sooner, then use the alkane naming rules and -ol.

2° alcoholsIUPAC (common)

CH3CHCH3propan-2-ol (isopropyl alcohol)

|or 2-propanol

OH

CH3CHCH2CH3butan-2-ol or 2-butanol

|

OH


Unit 6

Nomenclature of Alcohols

isopropyl alcohol

IUPAC: propan-2-ol

or 2-propanol

t-butyl alcohol

IUPAC: methylpropan-2-ol

ethylene glycol

IUPAC: ethane-1,2-diol

Which are primary? Secondary? Tertiary?


Unit 6

Nomenclature of Alcohols

1°? 2°? 3°? Give the IUPAC name of each.

Give a VB description of one of the O-H bonds.


Unit 6

Nomenclature of Alcohols

propylene glycol

glycerine, glycerol

IUPAC:propane-1,2,3-triol

phenol

IUPAC: phenol

Draw the line angle structure for

2-methyl-3-butyn-2-ol


Unit 6

Nomenclature of Alcohols

IUPAC:10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

What is the H-C-C bond angle for either of the “dashed” H’s?


Unit 6

Draw Line Angle and 3-D Structures


Unit 6

Give Condensed Structural Formula


Unit 6

Functional Groups - Review

alcohol

ether

alkene

R = alkyl group

- X

halide

alkyne

- C≡N

amine (1°)

nitrile


Unit 6

Functional Groups - Review

aldehyde

carboxylic acid

amide

ketone

ester

aromatic ring


Unit 6

Functional Groups

Circle and label each functional group.

fructose

threonine

γ-butyrolactone (GBL)

acetaminophen


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