LEC MOD 6 Flashcards
A compound that containing an -OH bonded to a tetrahedral carbon
- an alkyl derivative of H2O
- hydroxyl derivative of alkanes
Alcohol
Features of a tetrahedral carbon:
-4 attachments
-Angle 109.5 degress
-
are negatively charge ions found in alkaline
Hydroxide ions
alcohol structural characteristics:
2 atoms, 2 lone pair of electrons, bent structure; 104.5b degrees- capable of intermolecular bonding- due to hydrogen bonding -higher boiling point
Alcohol physical characteristics:
polar and nonpolar components;
alkyl=R=NP
Hydroxyl=OH=P
relationship of carbon chain with boiling point
Directly proportional
Solubility of Alcohol
Like Dissolves Like
- soluble in organic solvents
- depend on C number and length of NP chain and amount of OH
- C number = Solubility- inversely
- OH= Solubility- directly
Solubilityi based on stoker and smith
Stoker less than 3- soluble
Smith less than 6- soluble
As long as OH are not overpowered by C atoms
Acidity of alcohol and phenols
Weak Acids
Classification of Alcohols
classified by number of C atoms bonded to C and OH
Classification of Alcohols
classified by number of C atoms bonded to C and OH
General formula of primary alcohol
RCH2OH
General formula of Secondary alcohol
R2CHOH
General formula of tertiary alcohol
R3COH
slowing of chemical reaction due to different stearic bond.
Stearic Hindrance
Rules in nomenclature for common name:
- determine number of carbon atoms
- determine placement ofnumbering where OH is connected
- name carbon chain,
Nomenclature: term to add if there is something that is attached in the second carbon
ISO
Nomenclature: term to use when hydroxyl is connected to the second carbon atom in a butyl
SEC
Nomenclature: Term to use when hydroxyl is connected to second carbon atom in a tetrahydryl structure
TER
IUPAC NAMING SYTEM RULE:
SUFFIX: -ol
Rule 1: Identify parent chain which OH is attached
Rule 2: OH is the priority in numbering
Rule 3: Name and locate any other substituents present
compound containing more than 1 hydroxyl groups
Polyhydroxy alcohols
Nomenclature: suffixes for polyhydroxy alcohols (IUPAC)
- diol- 2 OH
- triol- 3 OH
RULES for naming polyhydroxy alcohols:
determine number of C atoms
- determine number of OH atoms
- add “e” before suffix
Nomenclature: suffixes for polyhydroxy alcohols (Common name)
Glycol - 2 OH
elimination of a molecule of water from adjacent carbon atoms gives an alkene as a product
Dehydration
most difficult to dehydrate and requires temperature as high as 180 degrees
primary alcohols
Undergo acid-catalyzed dehydration at lower temp
Secondary alcohols
undergo acid-catalyzed dehydration at temperatures slightly above room temp (20-24 degrees)
Tertiary alcohol
Dehydration is what kind of reaction?
Elimination reaction
rule that states that then major product in elimination is the alkene that has more alkyl groups bonded to it
Zaitsev rule
Alcohol to alkene is also a reversible chemical reaction according to what principle?
Le Chatelier’s Principle
a principle that establishes equilibrium in an event that certain stressors that are applied into the reaction are relieved
Le Chatelier’s Principle
a principle that establishes equilibrium in an event that certain stressors that are applied into the reaction are relieved
Le Chatelier’s Principle
stressors require for the conversion of alcohol to alkene:
Temp
Strong Acid
Combining of 2 molecules to form a larger molecule while liberating a small portion, usually in a form of water; 2 ROH - form water and ether
Condensation
Operational rules in oxidation and reduction of alcohols
Reduction= decrease C-O bonds and increase C-H bonds Oxidation= increase C-O bonds and decrease C-H bonds
replacement of C-H bonds with C-O bonds
Oxidation of alcohols
product of oxidation of alcohol
Carbonyl group- C=OH
oxidation of alcohols by classification
primary and secondary = readily oxidation
tertiary = resist oxidation
Oxidation of primary alcohol
ROH-R-CHO(aldehyde- RCOOH (Carboxylic acid)
oxidation of secondary alcohol
oxidized to ketones replacng 1C-H with 1C-O
Oxidation tertiary alcohol
prone to dehydation because ofacd-catalyst
oxygen leads production heat and light
Combustion
single product is obtained from which the halogen atom found only where the hydroxyl group is originally located
Halogenation
organic molecules containing a halogen atom.
Alkyl halides
IUPAC name of phenol
Benzenol
Commong or preffered name of phenol
Phenol
Old name of phenol
Carbolic Acid
Nomenclature for phenols
When substituents are added, the carbon with OH attached to it is considered to be numbered as 1; 1 is omitted from the name IUPAC
instead of numbers these are use instead for determining the placement of the substituent in the benzene ring
ortho, meta, para
o-1
m-2
p-3
phenol with OH
Hydroxyphenols
Nomenclature for hydroxyphenols
1,2 OH Catechol
1,3 OH Resorcinol
1,4 OH Hydroquinone
methylphenol are also called
cresols
rules for two or more substituents in phenol
- number to give the lowest possible numbers around the ring
- Alphabetize the substituent names
properties of phenol
Medicinal odor slightly soluble to water flammabale can't be dehydrated oxidized by strong oxidizers Halogenation (weak acids)
the weak acidity of phenols is due to?
the stability of phenoxide ion compared with an alkoxide ion
pKa and pH of phenol and Alcohol
Phenol-10
Alcohol- 16-18
pH phenol- 5-5
pH Alcohol- neutral
how many times does an oxygen atom in alcohol participate in single and double covalent bonda?
2-single
1-double
dehydration that produces alkene and water
Intramolecular dehydration
dehydration that produces ehter and water
Intermolecular dehydration
Temp required for producing alkene in dehydration
180
Temp required for producing ether in dehydration
140
