Chapter 5

Alcohols and alkyl halides and an introduction to reactions

Which functional group is shown? (R = rest of molecule, X = any halogen)

Alkane

Alkane is what type of functional group

Hydrocarbon

Naming of alkanes

Add: -ane

Which functional group is shown? (R = rest of molecule, X = any halogen)

Alkene

Alkene is what type of functional group?

Hydrocarbons

Naming of alkene:

Add: -ene

Which functional group is shown? (R = rest of molecule, X = any halogen)

Alkyne

What functional group is alkyne?

Hydrocarbon

Naming of alkyne

Add: -yne

Which functional group is shown? (R = rest of molecule, X = any halogen)

Alcohol

Generalized abbreviation of alcohol:

ROH

What type of functional group alcohol?

Simple oxygen heteroatomics

Naming of alcohols:

Add: -ol

Generalized abbreviation of alkyl halide:

RCl

Generalized abbreviation of sulfide:

RSR

Which functional group is shown? (R = rest of molecule, X = any halogen)

Ether

Generalized abbreviation of ether:

ROR

What functional group is ether?

Simple oxygen heteroatomics

Naming of ethers:

Add: -oxy - ane

Which functional group is shown? (R = rest of molecule, X = any halogen)

Epoxide

Generalized abbreviation of amine:

What type of functional group is epoxide?

Simple oxygen heteroatomics

Naming of epoxides:

Add: -ene oxide

Which functional group is shown? (R = rest of molecule, X = any halogen)

Haloalkane

What type of functional group is Haloalkane?

Halogen Heteroatomics

Naming of haloalkanes:

Add: halo-

Which functional group is shown? (R = rest of molecule, X = any halogen)

Aldehyde

Generalized abbreviation of aldehyde:

What kind of functional group are aldehydes?

Carbonyl Compounds

Naming of aldehyde:

Add: -al

Which functional group is shown? (R = rest of molecule, X = any halogen)

Ketone

Generalized abbreviation of ketone:

What type of functional group is a ketone?

Carbonyl Compounds

Naming of ketone

Add: -one

Which functional group is shown? (R = rest of molecule, X = any halogen)

Carboxylic Acid

Generalized abbreviation of Carboxylic acid:

What type of functional group is carboxylic acid?

Carbonyl Compounds

Naming of carboxylic acid:

Add: -oic acid

Which functional group is shown? (R = rest of molecule, X = any halogen)

Acid Anhydride

Generalized abbreviation for acid anhydride

What type of functional group is acid anhydride?

Carbonyl Compounds

Naming of acid anhydride:

Add: -oic anhydride

Which functional group is shown? (R = rest of molecule, X = any halogen)

Ester

Generalized abbreviation for ester

What type of functional group is ester?

Carbonyl Compounds

Naming of ester:

Add: -yl -oate

Which functional group is shown? (R = rest of molecule, X = any halogen)

Amide

Generalized abbreviation for amide

What type of functional group is amide?

Carbonyl Compounds

Naming of amide:

Add: -amide

Which functional group is shown? (R = rest of molecule, X = any halogen)

Acyl Halide

Generalized abbreviation for acyl halide

What type of functional group is acyl halide?

Carbonyl Compounds

Naming of acyl halide:

Add: -oyl halide

Which functional group is shown? (R = rest of molecule, X = any halogen)

Amine

Generalized abbreviation of Amine

RNH2

What type of functional group is amine?

Nitrogen-Based

Naming of amine:

Add: -amine

Which functional group is shown? (R = rest of molecule, X = any halogen)

Nitrile

Generalized abbreviation of nitrile:

RC(triple bond)N

What type of functional group is nitrile?

Nitrogen-Based

Naming of nitrile:

Add: -nitrile

Generalized abbreviation of nitroalkane:

RNO2

Which functional group is shown? (R = rest of molecule, X = any halogen)

Imine

What type of functional group is imine?

Nitrogen-Based

Naming of imine:

Add: -imine

Which functional group is shown? (R = rest of molecule, X = any halogen)

Isocyanate

What type of functional group is isocyanate?

Nitrogen-Based

Naming of isocyanate:

Add: -yl isocyanate

Which functional group is shown? (R = rest of molecule, X = any halogen)

Azo Compound

What type of functional group is azo compound?

Nitrogen-Based

Naming of azo compound:

Add: azo-

Which functional group is shown? (R = rest of molecule, X = any halogen)

Thiol

Generalized abbreviation of thiol:

RSH

What type of functional group is thiol?

Sulfur-Based

Naming of thiol:

Add: -thiol

Which functional group is shown? (R = rest of molecule, X = any halogen)

Arene

What type of functional group is arene?

Aromatic

Naming of arene:

add: -yl benzene

IUPAC Nomenclature of Alcohols

Named by identifying the longest straight carbon chain containing the -OH group.

The -ane suffix is replaced with -anol

The location of the -OH group on the chain is designed by a number

What takes priority when numbering the Cs in IUPAC Nomenclature of Alcohols

Alcohol Takes Priority

Halogens has same priority as methyl groups

What is the IUPAC name?

2,2-Dimethyl-1-propanol

What is the IUPAC name?

2-chloro-2-methylpentane

What is the difference between Primary Alcohols, Secondary Alcohols, and Tertiary Alcohols

Primary - The C connected to the alcohol is connected to 1 other carbon

Secondary - The C connected to the alcohol is connected to 2 other carbons

Tertiary - The C connected to the alcohol is connected to 3 other carbons

Alcohol and alkyl halide boiling point increase with

Stronger van der Waals forces

• Dipole-dipole

• Dipole / induced-dipole

• Induced-dipole / induced-dipole

Other than intermolecular forces what effects the boiling point of alcohols?

Amounts of carbons in the main chain (more carbons higher boiling point)

Branching (increased branching decreased boiling point)

Small alcohol are _ in water

Small alcohols are soluble in water

(Methyl and ethyl are considered small)

Formation of an alkyl halide from an alcohol and hydrogen halide reaction

What kinds of alcohol are most reactive toward hydrogen halides

Tertiary most reactive

Hammond’s Postulate

If two states are similar in energy, they are similar in structure

Step of SN1 Reaction with an alcohol as a reactant

1. Alcohol protonation (OH bonds with H)

2. Carbocation formation (H2O leaves)

3. Anion reaction with carbocation

Carbocation

A molecule in which a carbon atom has a positive charge and three

bonds

Hybridization of carbocation

sp2 hybridized (molecular geometry is trigonal planar)

pz orbital is empty and perpendicular to the bond

What type of carbocation is the most stabile

tertiary

In carbocations: alkyl groups provide _ inductive donation than hydrogens

In carbocations: alkyl groups provide MORE inductive donation than hydrogens

Hyperconjugation

‘Sigma bond to p orbital donation’

3 centers sharing 2 electrons

2 things that stabilize carbocations

• inductive donation by alkyl groups along the sigma bond

• hyperconjugation, a through space donation of electron density by bonds that are adjacent and parallel to the empty p orbital

SN1 reactions are fastest with what kind of alcohol?

Tertiary (it forms most stable carbocation)

Stereochemistry of SN1 mechanisms

Not stereospecific

(But an SN1 reaction gives products that partially invert. Leading to a mixture

of S and R products generally)

2 types of rearrangements in SN1 mechanism:

Hydride Shift

Methanide Shift (Alkyl Shift)