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chemistry > 17 - alcohols, esters and carboxylic acids > Flashcards

17 - alcohols, esters and carboxylic acids Flashcards

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1
Q

alcohols general formula

A

CnH2n+1OH

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2
Q

alcohols functional group

A

hydroxyl group, OH

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3
Q

naming alcohols

A

add -anol to stem
location of OH in name (propan-2-ol)

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4
Q

primary alcohol

A

an alcohol in which the carbon atom is bonded to the OH group is attached to one other carbon atom/alkyl group

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5
Q

secondary alcohol

A

an alcohol in which the carbon atom is bonded to the OH group is attached to two other carbon atoms/alkyl groups

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6
Q

tertiary alcohol

A

an alcohol in which the carbon atom is bonded to the OH group is attached to three other carbon atoms/alkyl groups

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7
Q

alcohols with two OH groups

A

-diol

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8
Q

alcohol properties

A

. higher boiling points than expected (H bonding)
. smaller alcohols are miscible in water (H bonding)
. alcohols are weaker acids than water
. have a small degree of dissociation

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9
Q

degree of dissociation

A

the extent to which a molecule of an acid ionises in a solvent to produce H+ ions or the extent to which a base produces OH- ions in a solvent

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10
Q

ethanol dissociation in water

A

C2H5OH <=> C2H5O- (ethoxide ion) + H+

. equilibrium position at left

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11
Q

more alkyl groups of an alcohol = stronger/weaker acid?

A

weaker acid

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12
Q

reactions to make alcohols

A

. electrophilic addition of steam to an alkene (H3PO4 catalyst)
C2H4 + H2O => C2H5OH

. oxidation of alkenes with cold, dilute, acidified potassium maganate to form a diol
C2H4 + H2O + [O] => HOCH2CH2OH

. nucleophilic substitution (hyrolysis) of a halogenoalkane by heating with NaOH
CH3CH2Br + NAOH => CH3CH2OH + NaBr

. reduction of an aldehyde (primary alcohol) or ketone (secondary alcohol) using a reducing agent
CH3CH2CHO + 2[H] => CH3CH2CH2OH
CH3COCH3 + 2[H] => CH3CH(OH) CH3

. reduction of a carboxylic acid using a reducing agent
CH3COOH + 4[H] => CH3CH2OH +H2O

. hydrolysis of an ester by heating with a dilute acid or alkali

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13
Q

reducing agent

A

. NaBH4
. LiAlH4

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14
Q

alcohol reactions

A

. combustion
. substitution to form a halogenoalkane
. reaction with a sodium metal
. esterification
. hydrolysis of esters
. dehydration
. oxidation

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15
Q

alcohol reactions: combustion

A

alcohol + oxygen => CO2 + H2O

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16
Q

alcohol reaction: substitution to form a halogenoalkane

A

alcohol + hydrogen halide => halogenoalkane + water

. in situ - in a reaction vessel
. heated under reflux
. haloalkane distilled off + collected as oily droplets

. HCl made in situ
. HBr made using KBr or conc. sulfuric acid
. SOCl2 can be used (HCl, SO2 formed)
. P can be used (HX, POX3), PCl3 needs heating

17
Q

alcohol reaction: reaction with sodium metal

A

alcohol + sodium => sodium alkoxide + hydrogen

. longer the hydrocarbon chain = less vigorous the reaction with sodium metal

18
Q

alcohol reaction: esterification

A

. a reaction of a carboxylic/ acyl chloride with an alcohol/phenol to produce an ester and small molecules
. carboxylic acid + alcohol <=> ester + water
. ‘alcohol-yl carboxylic acid- noate’

19
Q

alcohol reaction: ester hydrolysis

A

. heating under reflux with acid/base
. acid:
—-reversible
—-ester + water => carboxylic acid + alcohol
AND PRESENT AFTER REACTION

. alkali:
—-fully hydrolysed
—-not reversible reaction
—-ester + NaOH => alcohol + sodium salt

20
Q

alcohol reaction: dehydration

A

. type of elimination reaction
. reaction in which water is removed from larger molecules
. alcohol => (heat and catalyst) alkene + water
—–catalyst = Al2O3/pumic/conc. acid, hot
—–alcohol vapour

21
Q

alcohol reaction: oxidation

A

. K2Cr2O7 oxidises only primary and secondary alcohols
. primary - forms aldehyde, carboxylic acid, GREEN
. secondary - forms ketone, GREEN
. tertiary - nothing, REMAINS ORANGE

22
Q

reactions to make carboxylic acids

A

. primary alcohol + potassium magnate solution
. nitrile + HCl

23
Q

carboxylic acid, acidic properties

A

. weak acids
. CH3COO ethanoate ion
. usual acid reactions

24
Q

carboxylic acids, reduction

A

. LiAlH4 is reducing agent
. use [H] symbol instead
. primary alcohol + water is the product

chemistry (18 decks)

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