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organic chemistry reactions Flashcards

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1
Q

give chemical equation of dehydration of an ethanol by concentrated sulfuric acid. mention which type of organic reaction it is.

A

C2H5OH –conc. H2SO4–> C2H4 + H2O

elimination reaction

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2
Q

CH4 + Cl2 –…–> CH3Cl + HCl

What type of organic reaction is it? What condition should be filled in?

A

substitution

UV light

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3
Q

chemical equation of hydrolysis of C2H5Br by alkali, NaOH

A

C2H5Br + NaOH -> C2H5OH + NaBr

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4
Q

C2H5OH + [O] -> CH3CHO + H2O
word formula of CH3CHO
is the oxidation reaction partial or complete?
where does the [O] come from?

A

ethanal
partial
acidified potassium dichromate(VI) solution

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5
Q

chemical equation of the complete oxidation of ethanol

what condition enables this complete oxidation

A

C2H5OH + 2[O] -> CH3COOH + H2O

reflux with excess acidified potassium dichromate(VI)

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6
Q

chemical equation of the reduction of acetone(propanone)

usually warmed with …

A

CH3COCH3 + 2[H] -> CH3CH(OH)CH3

aqueous alkaline solution of sodium tetrahydridoborate, NaBH4

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7
Q

in CH4 + Cl2 –UV light–> CH3Cl + HCl as a reference,

initiation step of substitution reactions of alkanes eq

A

Cl2 –UV light–> 2Cl•

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8
Q

in CH4 + Cl2 –UV light–> CH3Cl + HCl as a reference,
propagation steps of substitution reactions of alkanes eq(s), including the formation of dichloromethane and trichloromethane.

A

Cl• + CH4 -> •CH3 + HCl
•CH3 + Cl2 -> CH3Cl + Cl•

CH3Cl + Cl• -> •CH2Cl + HCl
•CH2Cl + Cl2 -> CH2Cl2 (dichloromethane) + Cl•

CH2Cl2 + Cl• -> •CHCl2 + HCl
•CHCl2 + Cl2 -> CHCl3 (trichloromethane) + Cl•

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9
Q

in CH4 + Cl2 –UV light–> CH3Cl + HCl as a reference,

termination step of substitution reactions of alkanes eq

A

•CH3 + Cl• -> CH3Cl

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10
Q

addition of H2(g) to CH2=CH2 and any condition/s

A

CH2=CH2 + H2 –Ni catalyst–> CH3CH3

140°C

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11
Q

addition of steam to CH2=CH2 and any condition/s

A

C2H4 + H2O –conc.H3PO4 catalyst–> C2H5OH
330°C
6MPa

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12
Q

addition of HBr to CH2=CH2 and any condition/s

A

CH2=CH2 + HBr -> CH3CH2Br

room temperature

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13
Q

condition/s for addition of halogens to alkenes

A

room temperature

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14
Q

oxidation of alkenes by hot concentrated manganate(VII) solution memorise

A

primary alkenes have CO2 as product
secondary have product aldehyde RCH=O, then a carboxylic acid RCOOH
tertiary have product ketone RRC=O

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15
Q

chem eq for oxidation of 2-methylprop-1-ene by hot concentrated mangante(VII) solution. word formula of the special product

A

(CH3)2C=CH2 + 4[O] -> (CH3)2C=O + CO2 + H2O

propanone

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16
Q

CH3CH2Br + NaOH

A

-> CH3CH2OH + NaBr

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17
Q

nucleophilic substitution reactions in halogenoalkanes bisa pkai apa aja

A

aqueous alkali, OH-(aq);
cyanide ions, CN-(in ethanol);
ammonia, NH3(in ethanol)

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18
Q

CH3CH2Br + CN- condition?

A

-> CH3CH2CN + Br- heated under reflux

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19
Q

CH3CH2Br + NH3 and special product name and condition?

A

-> CH3CH2NH2 + HBr
ethylamine
halogenoalkane heated with an excess of NH3 dissolved in ethanol under pressure

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20
Q

CH3CHBrCH3 + NaOH(ethanol) and what kind of reaction is it

A

-> CH2=CHCH3 + H2O + NaBr

elimination

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21
Q

hydrolysis CH3CH2Br + H2O reflux

A

-> CH3CH2OH + HBr

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22
Q

alcohol + hydrogen halide

A

-> halogenoalkane + water

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23
Q

CH3CH2OH + HCl and condition, how the dry HCl gas can be obtained, how the halogenoalkane can be collected?

A

-> CH3CH2Cl + H2O
alcohol heated under reflux.
HCl gas made in situ (in the reaction vessel) using NaCl and concentrated h2so4
NaCl + H2SO4 -> NaHSO4 + HCl.
CH3CH2Cl distilled off from the reaction mixture and collected as oily droplets under water.

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24
Q

alcohol + SOCl2

A

-> halogenoalkane + HCl + SO2

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25
Q

C2H5OH + SOCl2 and condition

A

-> C2H5Cl + HCl + SO2
heated under reflux
note: HCl and SO2 in gaseous state so no need to distil the halogenoalkane as it is left

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26
Q

C2H5OH + PCl5, state of PCl5

A

–room temperature–> C2H5Cl + HCl + POCl3

solid

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27
Q

use of C2H5OH + PCl5 –room temperature–> C2H5Cl + HCl + POCl3

A

release of acidic HCl gas from this reaction can be used as a test for the -OH group. the HCl gas cause acidic ‘steamy fumes’ to be observed.

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28
Q

C2H5OH + PI3

A

-> C2H5I + H3PO3

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29
Q

alcohols’ substitution to form halogenoalkane can use whatwhat

A

hydrogen halide, SOCl2, phosphorus halides

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30
Q

alcohol + phosphorus(V) halide

A

-> halogenoalkane + HCl + POCl3

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31
Q

alcohol + phosphorus(III) halide

A

-> halogenoalkane + H3PO3

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32
Q

condition for alcohol + PCl3 substitution reaction

A

heating required

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33
Q

condition for alcohol + PBr3/PI3 substitution reaction

A

PBr3 PI3 made in situ using red phosphorus and Br2 or I2. these are warmed with the alcohol

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34
Q

C2H5OH + Na

A

-> C2H5ONa + H2

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35
Q

C2H5ONa word formula, acidic or basic

A

sodium ethoxide, basic

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36
Q

C2H5OH + Na-> C2H5ONa + H2

with ethanol, if the excess ethanol is evaporated off the reaction, what do u see

A

a white crystalline solid is left. this is the sodium ethoxide

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37
Q

for reaction of alcohol with Na metal, what is the trend of vigor relative to hydrocarbon chain?

A

the longer the hydrocarbon chain, the less vigorous the reaction

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38
Q

use of bromine water

A

to test the presence of the C=C bond in compounds. the compound to be tested is shaken with it. if it is unsaturated the bromine water will be decolorised.

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39
Q

carboxylic acid + alcohol and condition

A

ester + water

heated under reflux with a strong acid catalyst, usually concentrated h2so4.

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40
Q

CH3CH2COOH + C2H5OH

propanoic acid + ethanol

A

CH3CH2COOC2H5 + H2O

ethyl propanoate + water

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41
Q

esters can be hydrolysed by

A

heating under reflux with either an acid or a base

42
Q

refluxing esters with an acid chem eq
using CH3COOCH2CH3
what kind of reaction

A

CH3COOCH2CH3 + H2O CH3COOH + CH3CH2OH

hydrolysis

43
Q

refluxing esters with alkali NaOH chem eq
using CH3COOCH2CH3
what kind of reaction

A

CH3COOCH2CH3 + NaOH -> CH3COONa + CH3CH2OH

hydrolysis

44
Q

sodium salt of a carboxylic acid,

CH3COONa word formula

A

sodium ethanoate

45
Q

dehydration of alcohol method

A

alcohol vapour is passed over a hot catalyst of Al2O3 powder – pieces of porous pot or pumice also catalyse the reaction.

46
Q

dehydration of ethanol chem eq

A

C2H5OH –Al2O3 catalyst–> CH2=CH2 + H2O

47
Q

what kind of reaction is dehydration reaction

A

elimination

48
Q

oxidation of alcohol method

A

warmed with K2Cr2O7 solution acidified with dilute h2so4.

49
Q

propan-2-ol + [O] special product name

A

-> CH3COCH3 + H2O

propanone

50
Q

CH3CH2OH + [O], special product name

A

-> CH3COH + H2O

ethanal

51
Q

C2H4O + [O]

A

-> CH3COOH

52
Q

tertiary alcohol + [O] and observation

A

no reaction. solution remains orange due to Cr2O7 2- (aq)

53
Q

secondary alcohol + [O] and observation

A

-> ketone + H2O

orange solution turns green due to Cr2O7 2-(aq) as an oxidising agent and are themselves reduced into Cr3+(aq)

54
Q

primary alcohol + [O] and observation(explain)

A

-> aldehyde + H2O
orange solution turns green due to Cr2O7 2-(aq) as an oxidising agent and are themselves reduced into Cr3+(aq)
aldehyde formed can be further oxidised to form carboxylic acid when refluxed with excess acidified k2cr2o7

55
Q

aldehyde + [O]

A

-> carboxylic acid

56
Q

nitrile + HCl + H2O,
what kind of reaction,
condition

A

-> carboxylic acid + NH4Cl
hydrolysis
reflux nitrile with dilute HCl

57
Q

hexanenitrile chem formula

A

C5H11CN

58
Q

hydrolysis when appropriate nitrile refluxed with dilute HCl to form propanoic acid, chem eq

A

CH3CH2CN + HCl + H2O -> CH3CH2COOH + NH4Cl

59
Q

ethanoic acid in water chem eq

A

CH3COOH(aq) revsersible arrow CH3COO-(aq) + H+(aq)

60
Q

CH3COOH + NaOH

A

-> CH3COONa + H2O

61
Q

methanoic acid in water chem eq

A

HCOOH(aq) HCOO-(aq) + H+(aq)

62
Q

HCOOH(aq) + H2O(l)

A

(reversible arrow) HCOO-(aq) + H3O+(aq)

63
Q

CH3COOH + Mg balanced eq

A

2CH3COOH + Mg -> (CH3COO)2Mg + H2

64
Q

C2H5COOH + K2CO3

A

-> C2H5COOK + H2O + CO2

65
Q

reduction of carboxylic acids reducing agent

A

lithium tetrahydridoaluminate LiAlH4 in dry ether at room temperature

66
Q

reduction of ethanoic acid balanced chem eq

A

CH3COOH + 4[H] -> CH3CH2OH + H2O

67
Q

butanal structural formula

A

CH3CH2CH2CHO

68
Q

HCHO name

A

methanal

69
Q

butanone structural formula

A

CH3COCH2CH3

70
Q

CH3COCH2CH2CH3 name

A

pentan-2-one

71
Q

preparation of aldehyde

A

oxidation of primary alcohol by KCr2O7 solution acidified with dilute H2so4, heated gently. aldehyde made distilled off as soon as it forms in the reaction vessel.

72
Q

preparation of propanal word eq

A

propan-1-ol + [O] -> propanal + H2O

note: propan-1-ol because it’s primary alcohol to make aldehyde

73
Q

preparation of ketone

A

oxidation of a secondary alcohol by KCr2O7 solution acidified with dilute H2so4, heated gently. ketone made distilled off from reaction vessel

74
Q

preparation of propanone chem eq

A

CH3CH(OH)CH3 + [O] -> CH3COCH3 + H2O

75
Q

aldehyde + reducing agent

A

-> primary alcohol

76
Q

ketone + reducing agent

A

-> secondary alcohol

77
Q

reduction of aldehydes and ketones method

A

the reduction reaction is carried out by either:
- warming the aldehyde or ketone with an aqueous alkaline solution of sodium tetrahydridoborate NaBH4
- adding lithium tetrahydridoaluminate LiAlH4 dissolved in a dry ether, such as diethyl ether, at room temperature.
Note: LiAlH4 more powerful reducing agent than NaBH4.

78
Q

balanced eq of reduction of ethanal and propanone

A

Respectively,
CH3CHO + 2[H] -> CH3CH2OH
CH3COCH3 + 2[H] -> CH3CH(OH)CH3

79
Q

CH3CH2CHO + HCN
special product name
what kind of reaction
condition

A

-> CH3CH2CH(OH)CN
2-hydroxybutanenitrile
(nucleophilic) addition
HCN generated in situ by the reaction of NaCN and dilute H2SO4

80
Q

nitrile group

A

-C≡N

81
Q

hydrolysis of a nitrile group ionic eq andcondition

A

-CN + H+ + H2O -> -COOH + NH4+

refluxing with dilute HCl

82
Q

reduction of nitrile group ionic eq and condition

A

-CN + 4[H] -> -CH2NH2

carried out using sodium and ethanol

83
Q

carbonyl group

A

C=O

84
Q

testing for a carbonyl group in aldehydes and ketones can use test with?
positive result?
how to identify which aldehyde or ketone it is with the carbonyl group?
what kind of reaction?

A

2,4-DNPH
deep-orange precipitate
the precipitate formed can be purified by recrystallization and its melting point measured experimentally, identity of compound that precipitated out be found by referring to melting point data.
condensation.

85
Q

use structure of 2,4-DNPH on pg 238 to write out eq for the reaction of ethanal with 2,4-DNPH

A

compare ur ans to pg 239

86
Q

can carboxylic acids and esters be tested with 2,4-DNPH to test for carbonyl group? explain.

A

cannot. because they do not form precipitates.

87
Q

ketones when tested with Tollens’ reagent

A

no reaction. It remains a colorless mixture.

88
Q

aldehydes when tested with Tollens’ reagent

A

positive result: silver mirror inside test tube.

89
Q

ketones when tested with Fehling’s solution

A

no reaction. solution remains blue.

90
Q

aldehydes when tested with Fehling’s solution

A

positive result: blue solution turns to a red/orange ppt.

91
Q

silver mirror when testing with tollens’ reagent caused by

A

Ag atoms

92
Q

red/orange ppt when testing with fehling’s solution caused by

A

Cu+ ions

93
Q

CH3CO– group found in

A

methyl ketones and ethanal

94
Q

another name for tri-iodomethane

A

iodoform

95
Q

alkaline iodine solution can be used to test for? positive test?

A

for methyl ketones CH3CO– group and ethanol or secondary alcohols with an adjacent methyl group CH3CH(OH)– group.
a yellow ppt of tri-iodomethane.

96
Q

alkaline iodine solution test method

A

the reagent used is an alkaline solution of iodine, which is warmed together with the substance being tested.

97
Q

two steps of the reaction to form tri-iodomethane

A

Step 1, halogenation:
the carbonyl compound is halogenated – the three H atoms in the CH3 group replaced by I atoms
RCOCH3 –I2, NaOH(aq)–> RCOCI3

Step 2, hydrolysis:
the intermediate is hydrolysed to form the yellow ppt of tri-iodomethane, CHI3
RCOCI3 –NaOH(aq)–> RCOONa + CHI3

98
Q

the extra step in the reaction to form tri-iodomethane when testing for CH3CH(OH)– group

A

CH3CH(OH)– group is firstly oxidised by the alkaline iodine solution, forming methyl ketone RCOCH3

99
Q

State the reagent(s) and conditions needed for CH3(CH2)3Br to react to form CH3(CH2)3NH2

A

reagent(s): ammonia

condition(s): heat with under pressure or in a sealed tube

100
Q

State a reagent used to distinguish (CH3)3COH from CH3(CH2)2CH2OH. Desribe any observations.

A 
reagent: H+/Cr2O7 2-
observations with CH3(CH2)2CH2OH: solution changes color from orange to green
observations with (CH3)3COH : solution remains orange
101
Q

can sodium react with -co2h? with -oh?
Yesyes
NaHCO3 and other Na compounds only react with COOH but not with Oh. oh can only w Na metal.

A

okokok

chemistry 11b (10 decks)

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