Lecture 9 Flashcards by Emily Hagan

What is an aliphatic alcohol?

OH group is attached to a CHAIN.

OH group NOT attached to a carbon with a double bond (sp3 hybridized carbon).

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What is an enol?

OH group is attached to a carbon which is attached to a DOUBLE BOND.

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Describe the bonding in oxygen.

4sp3 hybrid orbitals.
TWO of the sp3 orbitals form SIGMA bonds to carbon and hydrogen atoms.
•The remaining two sp3 hybrid orbitals each contain an UNSHARED pair of electrons.

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In oxygen the remaining two sp3 hybrid orbitals each contain an UNSHARED pair of electrons, what does this influence?

Domain geometry about the hydroxyl oxygen atom which is approximately 109o.

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Common Names: Propan-1-ol

1- propanol

propyl alcohol

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Common Names: Propan-2-ol

2- propanol

isopropyl alcohol

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Common Names: Butan-1-ol

n- butanol

butyl alcohol

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Common Names: Butan-2-ol

sec- butanol

sec- butyl alcohol

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Common Names: 2-methyl-propan-1-ol

isobutyl alcohol

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Common Names: 2 Methyl- propane-2-ol

tert- butanol

tert- butyl alcohol

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Common Names: Ethane-1,2- diol

1,2- ethanediol

ethylene glycol

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Common Names: Propane- 1,2, diol

1,2 propanediol

propylene glycol

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Common Names: 1,2,3- propanetriol

propane-1,2,3 triol

glycerol/ glycerine

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Alcohol are polar compounds how does this effect their boiling points in comparison with hydrocarbons?

Higher boiling points because of hydrogen bonding.

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What other characteristics does hydrogen bonding give alcohols?

Lower alcohols- Water soluble.
Good solvents for a wide range of organic molecules.
Boiling point increases with the number of carbon atoms.

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Describe the properties of the Electron rich O in an alcohol.

Basic- Lone pair donors (Lewis bases) & proton acceptors (Bronsted- Lowry Bases)
Nucleophilic- Lone pair attacks electron deficient centres.

In the hydration of alkenes to form an alcohol, what is the reagent and conditions for the reaction?

Strong acid catalyst

Heat

How is anti- markovnikov product formed by hydration of an alkene?

BH3 is used because BORON is the most ELECTROPOSITIVE which is added to the molecule instead of Hydrogen. Hydrogen act as a H-. The OH group is added as the B is oxidised by the H2O2.

What is the anti- markovnikov product?

The MINOR product is now the major product which is the OPPOSITE the what Markovnikov predicted.

What is the reagent and reaction conditions for the substitution of an alkyl halide?

NaOH reacts with the alkene

Heat and H2O

To create a SIMPLE alcohol from the substitution of an alkyl halide, what does there need to be?

Nucleophilic source of oxygen, eg. NaOH.

What is a Grignard reagent?

R-+MgX (X= Br/ Cl)

What is an orgnolithium?

R-+Li

What is an organometal?

Negative Carbon + Positive Metal Ion

Carbon Is nucleophilic.

What happens in the reaction of the addition of an organometallic to aldehyde/ ketone.

When the aldehyde/ ketone reacts with the organometallic reagent it forms an unstable METAL SALT of the alcohol. Then H+/H2O is used to wash out the reagent to leave the alcohol.

What does NaBH4 reduce?

Aldehydes | Ketones

What does LiAlH4 reduce?

Carboxylic Acids Esters Aldehydes Ketones

What enzyme will turn alcohols into biological molecules? How?

CYP450 | Oxygen is taken in from the atmosphere and is turned in OH via radical reaction.

Alcohols can react via substitution reactions to form alkyl halides. What do they react with?

1. Thionyl Chloride 2. HX (Acids) 3. Phosphorus Halides

In the dehydration reaction- alkene is formed. What is the reaction conditions and reagent?

H2SO4 | 180oC

What is the enzyme (2) used in biological dehydration reactions to form an alkene?

Dehydroquinate | Dehydratase

What is needed for esterification?

Acid Catalyst

In biological esterification what enzyme is need?

Acyltransferases/ Esterases

Oxidation of Alcohols- What is a primary alcohol oxidised to? Reagents.

Primary Alcohol- (Na2Cr2O7/ H+) Aldehyde- (Na2Cr2O7/ H+)- Carboxylic Acid

Oxidation of Alcohols- What is a secondary alcohol oxidised to? Reagents.

Secondary Alcohol (Na2Cr2O7/ H+)- Ketone

Oxidation of Alcohols- What is a tertiary alcohol oxidised to? Reagents.

No Reaction

Describe practical details for the a primary alcohol being oxidised to aldehydes.

Alcohol dripped into warm solution- acidified Kr2Cr2O7. Aldehydes- low boiling points = no hydrogen bonding so distil off immediately. Not distilled off oxidise to a Carboxylic Acid Oxidise alcohol straight to acid- Reflux

In biological oxidation of alcohols what is the reagent used?

NAD+