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Organic Reactions Flashcards

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1
Q

-CN to -COOH reagents and conditions? 😇

A

Dilute H2So4

Heat under reflux

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2
Q

What is the powerful reducing agent that can reduce aldehydes…AND carboxylic acids??

A

LiAlH4 in dry ether

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3
Q

What is the weak reducing agent that can only reduce carbonyl compounds? (Ketones, aldehydes)

A

NaBH4 in ethanol/methanol

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4
Q

Nitrobenzene to phenylamine?

A
  1. Sn, conc Hcl, heat.

2. NaOH (aq)

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5
Q

-CN to -NH2?

A

LiAlH4 in dry ether

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6
Q

React alkene with dilute alkaline NaOH(aq), KMnO4 (aq) heat under reflux what do you get?

A

Diol

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7
Q

React alkene with H2So4 (aq) KMnO4 (aq) what do you get?

A

Terminal alkene - co2, h2o
Alkene with one alkyl group - aldehyde, further oxidation gives you carboxylic acid
Two alkyl groups - ketone

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8
Q

Nitration of benzene ring reagents and conditions GO

A

Conc HNo3
Conc H2SO4
Heat at 55 degrees

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9
Q

Halogenation of benzene ring reagents and conditions GO

A

X2

Fe / FeX3 or anhydrous AlX3

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10
Q

Alkene to alcohol r&c

A

H2O, H3PO4, 65 atm, 300 degrees

Lab method: add conc H2SO4 and heat with water

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11
Q

Phenol has -OH group which strongly activates the ring towards electrophilic substitution. It is 2,4-directing because saturated.

R&c for bromination of phenol vs benzene ring?

A

Phenol
Poly substituted: Br2 aqueous, room temp (non polar br2 in aqueous solvent, he fucking hates it and runs off to phenol, therefore poly sub)

Mono substituted: Br2 in CCl4

Benzene Ring:
X2, Fe / FeX3 or anhydrous AlX3

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12
Q

What are 2,4-directing groups? Saturated or unsaturated?

A

Saturated!!

Can be ring deactivating - halogens

Or ring activating :-) such as saturated alkyl groups.

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13
Q

What are the 3-directing groups?

A

Unsaturated (triple, double bonds) -» ring deactivating, electron withdrawing.

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14
Q

Alkene to alkane? 😀

A

H2 (g)
Ni catalyst
200 degrees

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15
Q

Phenol has -OH group which strongly activates the ring towards electrophilic substitution. It is 2,4-directing

R&c for nitration of phenol vs benzene ring?

A

Phenol:

Poly sub: Conc HNO3, room temperature

Mono sub: Dilute HNO3, room temperature

Benzene:

Conc HNO3 conc H2SO4 heat at 55 degrees

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16
Q

Why do we want to have CN?

A
  • step up reaction +1 C
  • change to amine
  • change to carboxylic acid
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17
Q

Alkyl halide to amine not through CN, how?

A

Excess NH3
Ethanolic medium
Heat in sealed tube

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18
Q

Alkyl halide react with CN, r&c?

A

Ethanolic KCN

HEAT UNDER REFLUX

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19
Q

Carbonyl compound react with CN, R&C?

A

HCN
SMALL amount of NaOH(aq) or NaCN(aq), as catalyst

NO FUCKING HEAT

20
Q

Alcohol to acyl chloride?

A

PCl3 / PCl5 / SOCl2
Room temp
Nucleo sub

21
Q

Alkene to alkyl halide?

A

HX (g) room temp

X2 (g/l) or x2 dissolved in CCl4 room temp

22
Q

Alcohol to alkyl halide?

A

HX (g) heat
PX3
PCl5 room temp
SOCl2 room temp

23
Q

Condensation to form esters

r&;c of alcohol + carboxylic acid?

A

Alcohol + carboxylic acid

Few drops of conc H2SO4 heat under reflux

24
Q

Condensation to form esters

r&c of alcohol + acyl chloride?

A

Room temp

25
Q

Condensation to form esters

r&c of PHENOL + carboxylic acid?

A

NaOH (aq)

26
Q

Condensation

Amide from acyl chlorides HOW?

A

Acyl chloride + substituent amine u want :-)

hcl comes out

27
Q

Hydrolysis of esters to alcohol and carboxylic acid

Needs??

A

h2o
Hcl (aq) or h2so4 (aq)
Heat under reflux

Reversible rxn unlike alkaline hydrolysis:
NaOH (aq) hear under reflux which is irreversible

28
Q

Alkyl halide to alcohol?

A

NaOH (aq) heat under reflux

not ethanolic!!! Or will become alkene!!

29
Q

Can aryl ketones be oxidised?

Reagents conditions? To what?

A

Yes.

H2SO4, KMnO4 (aq) heat under reflux

Gives you aryl carboxylic acids.

30
Q

Nitration of alkyl benzene?

A

Conc HNO3
Conc H2SO4
Heat at 30 degrees NOT 55

31
Q

Effect of amine on phenylamine?

A

Electron donating
Ring activating
Milder conditions
Poly substitution

32
Q

Acidic hydrolysis of amides gives ______?

Reagents and conditions?

A

carboxylic acids + ammonium ION!!!

H2O, Hcl (aq) or H2SO4 (aq) heat under reflux

33
Q

Alkaline hydrolysis of amides gives ______?

Reagents and conditions?

A

Carboxylate salt and ammoNIA

NaOH (aq) heat under reflux

34
Q

If NH2 is in presence of dilute H2SO4 heat under reflux??

A

It accepts a proton, it is a base. NH3+

35
Q

Oxidise primary alcohol to aldehyde

reagents and conditions?

A

H2so4
K2Cr2O7 (aq)
Heat with immediate distil

Mild oxidation

36
Q

Oxidise primary alcohol to carboxylic acid reagents and conditions?

A

H2SO4
KMnO4 (aq) or K2Cr2O7
Heat under reflux

Vigorous oxidation

37
Q

Oxidation secondary alcohol to ketones??

A

H2SO4
KMnO4 (aq)
Heat under reflux

38
Q

Oxidise tertiary alcohols?

A

Trick question. Doesnt happen.

39
Q

Phenol reacts with NaOH(aq) (aqueous so it can dissociate and be ACID) at room temp.

Type of reaction:
Products?

A

Acid-base reaction

Salt is formed (Metal replaces the OH) + H2O

40
Q

Carboxylic acids react with NaOH(aq**) to give?

A

RCOOH + NaOH -> RCOO-Na+ + H2O

41
Q

Phenols, carboxylic acids and alcohols react with reactive metals SUCH AS Na.

Type of reaction:
Products?

A

Acid METAL reaction

Salt + H2, colourless gas evolved extinguishes lighted splint with a pop sound

K and Mg also OK

42
Q

Reduce carboxylic acids with LiAlH4 in dry ether what do you get?

A

Alcohol + water.

43
Q

Methanoic Acid (HCOOH) and Ethanedioic Acid (COOH)2

Oxidation R&C and PRODUCTS

A

Acidified KMNO4 Heat Under Reflux

HCOOH + [O] -> CO2 + H2O
(COOH)2 + [O] -> 2CO2 + H2O

44
Q

Methanoic Acid (HCOOH) and Ethanedioic Acid (COOH)2

Dehydration R&C and PRODUCTS

A

Conc H2SO4 Heat

HCOOH -> CO + H2O
(COOH)2 -> CO2 + CO + H2O

45
Q

For HCOOH only

Oxidation by Fehling’s and Tollens’ reagent

A

HCOOH has aldehyde group (-CHO), easily oxidised, produces brickred ppt of Cu2O with Fehling’s reagent, silver mirror with Tollens’ reagent.

DOES NOT FORM acyl chloride HCOCl, highly unstable, decomposes to give CO and HCL

46
Q

Phenol acid-base reagents and conditions?

A

NaOH (aq)

ROOM TEMP ✨✨

Chemistry (8 decks)

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