Organic Reactions Flashcards
-CN to -COOH reagents and conditions? 😇
Dilute H2So4
Heat under reflux
What is the powerful reducing agent that can reduce aldehydes…AND carboxylic acids??
LiAlH4 in dry ether
What is the weak reducing agent that can only reduce carbonyl compounds? (Ketones, aldehydes)
NaBH4 in ethanol/methanol
Nitrobenzene to phenylamine?
- Sn, conc Hcl, heat.
2. NaOH (aq)
-CN to -NH2?
LiAlH4 in dry ether
React alkene with dilute alkaline NaOH(aq), KMnO4 (aq) heat under reflux what do you get?
Diol
React alkene with H2So4 (aq) KMnO4 (aq) what do you get?
Terminal alkene - co2, h2o
Alkene with one alkyl group - aldehyde, further oxidation gives you carboxylic acid
Two alkyl groups - ketone
Nitration of benzene ring reagents and conditions GO
Conc HNo3
Conc H2SO4
Heat at 55 degrees
Halogenation of benzene ring reagents and conditions GO
X2
Fe / FeX3 or anhydrous AlX3
Alkene to alcohol r&c
H2O, H3PO4, 65 atm, 300 degrees
Lab method: add conc H2SO4 and heat with water
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?
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
What are 2,4-directing groups? Saturated or unsaturated?
Saturated!!
Can be ring deactivating - halogens
Or ring activating :-) such as saturated alkyl groups.
What are the 3-directing groups?
Unsaturated (triple, double bonds) -» ring deactivating, electron withdrawing.
Alkene to alkane? 😀
H2 (g)
Ni catalyst
200 degrees
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?
Phenol:
Poly sub: Conc HNO3, room temperature
Mono sub: Dilute HNO3, room temperature
Benzene:
Conc HNO3 conc H2SO4 heat at 55 degrees
Why do we want to have CN?
- step up reaction +1 C
- change to amine
- change to carboxylic acid
Alkyl halide to amine not through CN, how?
Excess NH3
Ethanolic medium
Heat in sealed tube
Alkyl halide react with CN, r&c?
Ethanolic KCN
HEAT UNDER REFLUX
Carbonyl compound react with CN, R&C?
HCN
SMALL amount of NaOH(aq) or NaCN(aq), as catalyst
NO FUCKING HEAT
Alcohol to acyl chloride?
PCl3 / PCl5 / SOCl2
Room temp
Nucleo sub
Alkene to alkyl halide?
HX (g) room temp
X2 (g/l) or x2 dissolved in CCl4 room temp
Alcohol to alkyl halide?
HX (g) heat
PX3
PCl5 room temp
SOCl2 room temp
Condensation to form esters
r&;c of alcohol + carboxylic acid?
Alcohol + carboxylic acid
Few drops of conc H2SO4 heat under reflux
Condensation to form esters
r&c of alcohol + acyl chloride?
Room temp
Condensation to form esters
r&c of PHENOL + carboxylic acid?
NaOH (aq)
Condensation
Amide from acyl chlorides HOW?
Acyl chloride + substituent amine u want :-)
hcl comes out
Hydrolysis of esters to alcohol and carboxylic acid
Needs??
h2o
Hcl (aq) or h2so4 (aq)
Heat under reflux
Reversible rxn unlike alkaline hydrolysis:
NaOH (aq) hear under reflux which is irreversible
Alkyl halide to alcohol?
NaOH (aq) heat under reflux
not ethanolic!!! Or will become alkene!!
Can aryl ketones be oxidised?
Reagents conditions? To what?
Yes.
H2SO4, KMnO4 (aq) heat under reflux
Gives you aryl carboxylic acids.
Nitration of alkyl benzene?
Conc HNO3
Conc H2SO4
Heat at 30 degrees NOT 55
Effect of amine on phenylamine?
Electron donating
Ring activating
Milder conditions
Poly substitution
Acidic hydrolysis of amides gives ______?
Reagents and conditions?
carboxylic acids + ammonium ION!!!
H2O, Hcl (aq) or H2SO4 (aq) heat under reflux
Alkaline hydrolysis of amides gives ______?
Reagents and conditions?
Carboxylate salt and ammoNIA
NaOH (aq) heat under reflux
If NH2 is in presence of dilute H2SO4 heat under reflux??
It accepts a proton, it is a base. NH3+
Oxidise primary alcohol to aldehyde
reagents and conditions?
H2so4
K2Cr2O7 (aq)
Heat with immediate distil
Mild oxidation
Oxidise primary alcohol to carboxylic acid reagents and conditions?
H2SO4
KMnO4 (aq) or K2Cr2O7
Heat under reflux
Vigorous oxidation
Oxidation secondary alcohol to ketones??
H2SO4
KMnO4 (aq)
Heat under reflux
Oxidise tertiary alcohols?
Trick question. Doesnt happen.
Phenol reacts with NaOH(aq) (aqueous so it can dissociate and be ACID) at room temp.
Type of reaction:
Products?
Acid-base reaction
Salt is formed (Metal replaces the OH) + H2O
Carboxylic acids react with NaOH(aq**) to give?
RCOOH + NaOH -> RCOO-Na+ + H2O
Phenols, carboxylic acids and alcohols react with reactive metals SUCH AS Na.
Type of reaction:
Products?
Acid METAL reaction
Salt + H2, colourless gas evolved extinguishes lighted splint with a pop sound
K and Mg also OK
Reduce carboxylic acids with LiAlH4 in dry ether what do you get?
Alcohol + water.
Methanoic Acid (HCOOH) and Ethanedioic Acid (COOH)2
Oxidation R&C and PRODUCTS
Acidified KMNO4 Heat Under Reflux
HCOOH + [O] -> CO2 + H2O
(COOH)2 + [O] -> 2CO2 + H2O
Methanoic Acid (HCOOH) and Ethanedioic Acid (COOH)2
Dehydration R&C and PRODUCTS
Conc H2SO4 Heat
HCOOH -> CO + H2O
(COOH)2 -> CO2 + CO + H2O
For HCOOH only
Oxidation by Fehling’s and Tollens’ reagent
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
Phenol acid-base reagents and conditions?
NaOH (aq)
ROOM TEMP ✨✨
