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A level Chemistry > Organic Synthesis > Flashcards

Organic Synthesis Flashcards

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1
Q

Clean blue flame

A

Alcohol or ester

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2
Q

Yellow flame

A

Alkane

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3
Q

Smoky yellow flame

A

Unsaturated/aromatic compound

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4
Q

Insoluble in water; two layers form

A

London forces only in hydrocarbon

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5
Q

Partially soluble forming an emulsion

A

H-bonds in long chain alcohol or p.d.-p.d. or leave to settle

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6
Q

Soluble Homogenous Liquid

A

H-bonds in alcohol or acid

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7
Q

> C=C< test 1

A

Shake with Br water at room temp,
Orange–> colorless
RCH=CHR + HOBr –> RCHBrCHOHR (Bromoalcohol)

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8
Q

> C=C< test 2

A

Shake with dil. H2SO4 + KMnO4
Purple–> colourless (possible brown ppt)
RCH=CHR + [O] + H2O –> RCHOHCHOHR (Alkanediol)

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9
Q

C-Cl
C-Br
C-I

A

Use ethanol as solvent. warm with NaOH(aq). Acidify with dil. HNO3 and add AgNO3. ppt produced. add dil NH3, then conc. NH3

White ppt soluble in dil. NH3
Cream ppt soluble in conc. NH3
Yellow ppt insoluble in either

RCH3X + OH- –> RCH3OH + X-
X- + Ag- –> AgX (ppt)

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10
Q

C-OH test 1

A

PCl5, Anhydrous, room temp, test gas produced with conc. NH3

Steamy fumes produce white smoke with NH3

R-OH + PCl5 –> R-Cl + POCl3 + HCl
HCl + NH3 –> NH4Cl, white smoke

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11
Q

C-OH test 2

A

K2CR2O7 + Dil. H2SO4 (Acidified dichromate)

Orange sol. –> green/blue-green

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12
Q

C-OH test 3

A

Add small piece of sodium

Effervescence, sodium disappears, white solid produced

CH3CH2OH + Na –> CH3CH2O-Na+ H2(g)

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13
Q

Carbonyl Group Test

A

2,4-DNP + few drops conc. H2SO4 warm

Orange sol. forms orange/red crystals

2,4-dinitrophenylhydrazine–> 2,4-dinitrophenylhydrazone
practice mechanism

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14
Q

Test 1 to differentiate between aldehyde and ketone

A

Fehlings solution; add Fehlings A (Cu2+) and Fehlings B (tartrate) and warm

Blue solution–>red ppt

Cu2+(aq) + e- –> Cu+(s), therefore reducing group present, aldehyde
Aldehyde –> Carboxylic Acid

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15
Q

Test 2 to differentiate between aldehydes and ketones

A

Tollens Reagent; AgNO3(aq) + dil NH3 add to unknown and warm,

Colourless solution forms silver mirror on test tube sides

[Ag(NH3)2]+(aq) + e- –> Ag(s) + 2NH3(aq)
reducing agent present=aldehyde,
aldehyde–> carboxylic acid

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16
Q

Test for methyl ketone

A

Iodoform test; I2 crystal, shake with unknown, add dil. NaOH dropwise & warm

Pale yellow crystals with antiseptic smell

Crystals = CHI3, iodoform
RCHOHCH3 + [O] –> RCOCH3 + H2O, Methyl ketone

RCOCH3 + 3I2 + 4NaOH –> RCOO-Na+ + CHI3 + 3NaI + 3H2O
Sodium carbodylate salt + iodoform

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17
Q

RCOOH

A

litmus turns red

Add to carbonate e.g. NaHCO3, at room temp,
Effervescence, limewater turns milky
RCOOH –> RCOO- + H+
HCO3- + H+ –> H2O + CO2

Estherification; ROH, few drops of conc. H2SO4 and warm
Sweet smell
RCOOH + ROH –> RCOOR + H2O

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18
Q

Substitution: Nucleophilic

A

Halogenoalkane; RX

RX + OH- –> ROH + X-, alcohol

RX + CN- –> RCN + X-, nitrile (note, if carbon chain extends by, this probably has something to do with it

RX + NH3 –> RNH2 + HX, amine

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19
Q

Substitution: Electrophilic

A

Aromatics;

Benzene + HNO3/H2SO4 –> Nitrobenzene

Benzene + Cl2 AlCl3/FeCl3 –> Chlorobenzene

Benzene + RX/AlCl3 –> Alkyl benzene

Benzene + RCOCl/AlCl3 –> acylbenzene

20
Q

Substitution: Free Radical

A

Alkanes + Halogen, X

Alkane + X2/UV –> Halogenoalkane

21
Q

Addition: Nucleophilic

A

Carbonyl compounds + HCN –> Hydroxynitryl

22
Q

Addition: Electrophilic

A

Alkene + Cl2 –> dichloroalkane

Alkene + HCl –> Chloroalkane

23
Q

Addition: Polymerisation

A

Alkenes –> polymers

24
Q

Oxidation: alkene

A

reagents and conditions: KMnO4 and dil NaOH(cold)/Diol

Product: Diol

25
Q

Oxidation: Alcohol

A

reagents and conditions: distillation, acidified dichromate, K2Cr2O7 + dil. H2SO4

Product: Aldehyde

26
Q

Oxidation: Aldehyde

A

Reagents and conditions: Reflux, acidified dichromate

Product: Carboxylic Acid

27
Q

Reduction: Alkene

A

Reagents and conditions: Heated nickel catalyst or room temp Pt catalyst, H2 Hydrogenation

Product: Alkane

28
Q

Reduction: Aldehyde

A

Reagents and conditions: NaBH4 or LiAlH4 sol. room temp

Product: Alcohol

29
Q

Reduction: Carboxylic acid

A

Reagents and conditions: LiAlH4, dry ether followed by dil. HCl Hydrolysis

Product: alcohol

30
Q

Reduction: Ketone

A

Reagents and conditions: NaBH4 sol. room temp

Products: Secondary alcohol

31
Q

Reduction: Nitrobenzene

A

Reagents and conditions: Sn and conc. HCl, heat under reflux followed by dil. NaOH

Products: Phenylamine

32
Q

Reduction: Nitrile

A

Reagents and conditions: LiAlH4, dry ether, followed by dil. NaOH

Products: Amine

33
Q

Carboxylic acid + alcohol

A

Reagents and conditions: Conc. H2SO4, anhydrous, warm

Product: Ester

34
Q

Acid Chloride + H2O/ROH/NH3/RNH2

A

Reagents and conditions: add the two at room temp or warmed

Product: Carboxylic acid, ester, (N-substituted) amide

35
Q

Hydrolysis: Ester

A

Reagents and conditions: Strong acid/based hydrolysis under reflux

Products: Carboxylic acid + alcohol

36
Q

Hydrolysis: Nitrile

A

Reagents and conditions: dil. HCl or dil. NaOH, under reflux

Products: Carboxylic acid + Carboxylate salt

37
Q

Elimination

A

Reagents and conditions: Ethanolic KOH under reflux

Products: Alkene

38
Q

Acid/Base: Alcohol + Na

A

Reagents and conditions: room temp, small piece of sodium

Products: Sodium Alkoxide

39
Q

Acid/Base: Carboxylic acid + alkali

A

Reagents and conditions: room temp

Products: carboxylate salt + water

40
Q

Acid/Base: Amine + HCl

A

Reagents and conditions: room temp

Products: alkyl ammonium salt

41
Q

Decreasing carbon skeleton: Iodoform

A

e. g.1: primary alcohol, CH3CH2OH + 3I2 + 4NaOH –> HCOO-Na+ + CHI3 + 3NaI + 3H2O
e. g.2: methylketone, CH3COCH3 + 3I2 + 4NaOH –> CH3COO-Na+ + CHI3 + 3NaI + 3H2O

42
Q

Decreasing Carbon skeleton: Ester hydrolysis

A

RCOOR + H2O (dil.acid or alkali, reflux) —> RCOOH/RCOO-Na+ + ROH

43
Q

Increasing carbon skeleton by one

A

HCN + Carbonyl compound
RCOR + HCN (KCN + alkaline buffer or ethanol) –> RCOH(CN)R

KCN + halogenoalkane
RCl + KCN (ethanol, reflux) –> RCN + KCl

44
Q

Increasing carbon skeleton by one or more: Alkylation

A

Catalyst AlCl3 to produce electrophile
AlCl3 + RCl –> AlCl4- + R+

Electrophilic addition
C6H6 + R+ –> C6H5R + H+

45
Q

Increasing carbon skeleton by one or more: acylation

A

Catalyst AlCl3 to produce electrophile
AlCl3 + RCOCl –> AlCl4- + RCO+

Electrophilic addition
C6H6 + RCO+ –> C6CH5COR + H+

A level Chemistry (4 decks)

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