Alcohols Flashcards Preview

Organic Chemistry > Alcohols > Flashcards

Flashcards in Alcohols Deck (26):
1

General Formula

R-OH

2

Nomenclature IUPAC

-e of alkane root is changed to -ol

3

Nomenclature Common Name

name alkyl group as a derivative and followed by alcohol

ex: ethyl alcohol

4

When alcohol is NOT the highest prority group, it is named as a substituent with the prefix ____

hydroxy-

5

Phenols

hydroxyl groups attached to aromatic rings

the hydroxyl H is particularly acidic due to the resonance

6

When benzene rings contain two substituents, two groups on ADJACENT carbons are called ________ and two groups SEPERATED by a carbon are called ______. Two groups on OPPOSITE sides of the ring are called _____

ortho

meta

para

7

One of the prominent properties of alcohols is that tey are capable of _________ which results in higher melting and boiling points.

Molecules with more than one hydroxyl group show greater degrees of ______

hydrogen bonding

hydrogen bonding

8

Hydrogen Bond

induction from oxygen pulls electrons away from hydrogen to make + charge on H and - charge on O which then leads to a noncovalent bond between the H and O.

9

Strong acids have high ____ values and low ____ values meaning that _____ are the most acidic alcohols.

This is because of the _______ , the negative charge on the oxygen is stabilized to create an anion like environment.

Ka

pKa

phenols

resonance stabilization

10

The presence of other substituents on the ring effect the ____, ____ and _______. Electron withdrawing groups ____ acidity while electron donating groups _____ acidity.

acidity, boiling point, melting point

increase

decrease

11

The presence of more alkyl groups in non aromatic alcohols produce _____ acidic molecules as the alkyl groups _____ electron density and ____ the negative charge.

Conversely, they ____ positive charge explaining why more substituted carbocations have higher stability than less substituted carbocations.

less


increase

destabilize

stabilize

12

PCC

anhydrous oxidant

oxidizes Primary Alcohols into Aldehydes
oxidized Secondary Alcohols to Ketones



does this as it lacks the water needed to hydrate the aldehyde

13

With other oxidizing agents, aldehydes are hydrated to form ______ whcih can then be oxidized to ____

geminal diols

carboxylic acids

14

Tertiary alcohols cannot be oxidized because they are already as oxidized as they can be without ______

breaking a C-C bond

15

Sodium/Potassium Dichromate Salts

strong oxidizing agent

Primary Alcohol goes to Carboxylic Acid
Secondary Alcohol to Ketone

16

Jones Oxidation

Chromium Trioxide in Sulfuric Acid and Acetone, strongest oxidation

Primary Alcohols to Carboxylic Acids
Secondary Alcohols to Ketones

17

Hydroxyl groups of alxohols are ____ leaving groups

poor

18

Mesylate

compound with the functional group SO3CH3 derived from methansulfonic acid

alcohol + base + methylsulfonyl chloride

19

Tosylate

compound with the functional group -SO3C6H4CH3 derived from toluenesulfonic acid to produce an ester

alcohol + p-toluenesulfonyl chloride

20

Mesyl and TOsyl groups make the hydroxyl of an alcohol a ______ leaving group and serve as ____ groups.

better

protecting

21

Acetal

formed as a protecting group between an aldehyde/ketone with either: 1) two equivalents of alchol 2) a diol

Primary Carbons with 2 OR groups and a Hydrogen


do not react with reducing agents like LiAlH4 to protect the aldehyde/ketone until deprotection

22

Ketals

formed as a protecting group between an aldehyde/ketone with either: 1) two equivalents of alchol 2) a diol


Secondary Carbons with 2 OR groups

do not react with reducing agents like LiAlH4 to protect the aldehyde/ketone until deprotection

23

Quinone

phenols treated with oxidizing agents

the OH becomes a carbonyl

named by indicating position of carbonyls numerically and adding the name quinone to the parent phenol

not necessarily always aromatic

serve as electron acceptors

24

Phylloquinone

vitamin K1

important in photosynthesis and carboxylation of clotting factors

25

Hydroxyquinones

share the same ring and carbonyl backbone as quinone but have one or multiple hydroxyls added

behave like quinones with electron donating groups making them slightly less electrophillic

named by numbering position of hydroxyl group, total number of hydroxyls in prefic and the substituent name hydroxy

26

Ubiquinone

coenzyme Q

biologically active quinone

electron carrier most oxidized form and reduced to uniquinol when accepting electrons

long alkyl chain allows it to be lipid soluble