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Reaction: ???

H2C=CH2 -----> H3CCH3

reagents & conditions:??
Reaction: Reduction

H2C=CH2 + ?? -----> H3CCH3

reagents & conditions: H2, Ni/Pt Catalyst , Heat
Reaction: ???

CH2(OH)CH3 -----> H2C=CH2

reagents & conditions:??
Reaction: dehydration

CH2(OH)CH3 -----> H2C=CH2

reagents & conditions: 
1. Al2O3Heat
2. Excess Conc. H2SO4, 170oC
Reaction: Reduction

?? -----> ???


reagents & conditions: NaBH4 in methanol, Room temp
Reaction: Reduction

Carbonyl (-C=O) -----> 1°/2° Alcohol (-OH)


reagents & conditions: NaBH4 in methanol, Room temp
Reaction: ???

CH2ClCH3 -----> ??

reagents & conditions: NaOH(Aq), Heat
Reaction: Nucleophilic Substitution

CH2ClCH3 -----> CH2(OH)CH3

reagents & conditions: NaOH(Aq), Heat
Reaction: ???

CH3CH2Cl -----> CH3CH2CN

reagents & conditions:???
Reaction: Nucleophilic Substitution

CH3CH2Cl -----> CH3CH2CN

reagents & conditions:Aq. Alcoholic KCN/NaCN , Warm
Reaction: ???

Nitrobenzene -----> Phenylamine

reagents & conditions:???
Reaction: Reduction

Nitrobenzene -----> Phenylamine

reagents & conditions: Sn, Conc. HCl, Reflux
add NaOH
Reaction: ???

CH2ClCH3 -----> ??

reagents & conditions: Alcoholic NaOH
Reaction: Elimination

CH2ClCH3 -----> H2C=CH2 + HCl

reagents & conditions: Alcoholic NaOH
Reaction: Reduction

?? -----> ???
(3 responses)

reagents & conditions: H2Ni/Pt Catalyst , Heat
Reaction: Reduction

1. Alkene -----> Alkane
2. Nitrile (-CN) -----> Primary Amine (-CH2NH2)
3. Carbonyl (-C=O) -----> 1°/2° Alcohol (-OH)


reagents & conditions: H2, Ni/Pt Catalyst , Heat
Reaction: ??? 

CH2(OH)CH3 -----> CH2ClCH3

reagents & conditions: ???
(3 responses)
Reaction: Nucleophilic Sub.

CH2(OH)CH3 -----> CH2ClCH3

reagents & conditions:
1. Anhydrous PCl5
2. Anhydrous PCl3
3. Anhydrous SOCl
Reaction: Reduction

?? -----> ???
(3 responses)

reagents & conditions: LiAlH4, Room temp
Reaction: Reduction

1. Carboxylic Acid (-COOH) -----> 1° Alcohol
2. Nitrile (-CN) -----> Primary Amine (-CH2NH2)
3. Carbonyl (-C=O) -----> 1°/2° Alcohol (-OH)

reagents & conditions: LiAlH4, Room temp
Functional Group Test!

Phenol + NaOH (Aq)

Observations: ?? 
Rxn:??
Functional Group Test!

Phenol + NaOH (Aq)

Observations: 
Insoluble Phenol dissolves to form colourless soln
Rxn:
Acid-Base neutralisation 
Functional Group Test!

Warm cpd w NaOH(Aq)
cool.
Acidify w dil. HNO3
Add AgNO3(Aq)

Observations: ?? 
Rxn: R-X + OH--> ??
Functional Group Test!

Observations:
AgCl -> WHITE ppt (AgCl)
AgBr -> CREAM ppt (AgBr)
AgI -> YELLOW ppt (AgI)

Rxn: R-X + OH- --> ROH + X-
Reaction: ??? 

CH3COOH -----> CH3COCl

reagents & conditions: ???
(2 responses)
Reaction: Nucleophilic Sub.

CH3COOH -----> CH3COCl

reagents & conditions: 
1. Anhydrous PCl5
2. Anhydrous PCl3  
Functional Group Test!

Amine Salt + NaOH (Aq)
Warm gently.

Observations: ?? 
Rxn: 
CH3NH3+ + OH- ---> ???
C6H5NH3++ OH- ---> ???
Functional Group Test!

Observations:
For volatile amine: effervecence gas which turns damp red litmus blue

For non-volatile amine (5C/phenylamine): organic layer separates out


Rxn: 
CH3NH3+(aq) + OH-(aq) --> CH3NH2(g) + H2O(l)
C6H5NH3++ OH- ---> C6H5NH2(l) + H2O(l)
Reaction: ???

H2C=CH2 -----> BrH2CCH2Br

reagents & conditions: ??
observations: ??
Reaction: Electrophilic Addition

H2C=CH2 -----> BrH2CCH2Br

reagents & conditions: Br2 in CCl4
observations: Br2 decolourises
Functional Group Test!

Ammonium Salt + NaOH(Aq)
Warm gently.

Observations: ?? 
Rxn: 
NH4++ OH- ---> ???
Functional Group Test!

Observations: A gas that turns moist red litmus blue (NH3)
Rxn: 
NH4++ OH- ---> NH3(g) + H2O
Reaction: Electrophilic Addition

Phenol -----> ?-bromophenol +??

reagents & conditions: ??
observations: ??
Reaction: Electrophilic Addition

Phenol -----> 2/4-bromophenol + HBr

reagents & conditions: Brin CCl4
observations: Brdecolourises
Reaction: Electrophilic Sub.

Benzene -----> Bromobenzene

reagents & conditions: ???
observations: ???
Reaction: Electrophilic Sub.

Benzene + Br2 -----> Bromobenzene + HBr

reagents & conditions: Br2, FeBr3/AlBr3 catalyst 
observations: Br2 decolourises, white fumes formed
Reaction: Electrophilic Add.

H2C=CH-----> CH3CH2Cl

reagents & conditions: ???
observations: ???
Reaction: Electrophilic Add.

H2C=CH-----> CH3CH2Cl

reagents & conditions: HCl/Hbr, Anhydrous
observations: -

*Apply Markovnikov's Rule
Reaction: Electrophilic Add.

H2C=CH-----> CH3CH2OH

reagents & conditions: ???
observations: ???
Reaction: Electrophilic Add.

H2C=CH-----> CH3CH2OH

reagents & conditions:
1. Add cold conc. H2SO4
2. Add water & warm


observations:-
Reaction: Reduction

Phenylamide C6H5CONH2 -----> C6H5CH2NH2

reagents & conditions: ???
Reaction: Reduction

Phenylamide C6H5CONH2 -----> C6H5CH2NH2

reagents & conditions: LiAlH4 in dry ether, rtp
Reaction: Electrophilic Addition

*phenol -----> ???

reagents & conditions: Br2(Aq)
observations: ???

*applicable to phenylamine too 
Reaction: Electrophilic Addition

phenol + 3Br-----> 2,4,6-tribromophenol + 3HBr

reagents & conditions: Br2(Aq)
observations: decolourisation of Br2, white ppt (2,4,6-tribromophenol) formed

white fumes 


*applicable to phenylamine too
Reaction: Free radical sub.

H3CCH3 +??? -----> BrH2CCH3 +HBr

reagents & conditions: ???
observations: ???
Reaction: Free radical sub.

H3CCH3 + Br2 -----> BrH2CCH3 +HBr

reagents & conditions: Br2, UV light
observations: Bromine decolourises to form white fume of HBr
Reaction: ???

CH3CH2Cl -----> CH3CH2NH2

reagents & conditions: ???
Reaction: nucleophilic sub.

CH3CH2Cl -----> CH3CH2NH2

reagents & conditions: excess NH3(g), heat in sealed tube
Functional Group Test!

Fehling's Solution

Reagents & Conditions: ???

Observations: 
aliphatic aldehyde (RCHO) ---> ???
aromatic aldehyde (C6H5CHO) ---> ???
Functional Group Test!

Fehling's Solution

Reagents & Conditions: alkaline Cu2+ tartrate, warm

Observations: 
aliphatic aldehyde (R-CHO) ---> reddish-brown ppt (Cu2O)

CH3CHO + 2Cu2+ + 5OH-> CH3COO- + Cu2O + 3H2O

aromatic aldehyde (C6H5CHO) ---> no rxn
Reaction: Nucleophilic Substitution

?? + ??? -----> CH3CONHCH2CH3 + HCl

reagents & conditions: ??
Reaction: Nucleophilic Substitution

CH3COCl + NH2CH2CH3 -----> CH3CONHCH2CH+ HCl

reagents & conditions: -
Functional Group Test!

Tollen's reagent

Reagents & Conditions: ???

Observations: 
aliphatic aldehyde (RCHO) ---> ???
aromatic aldehyde (C6H5CHO) ---> ???
Functional Group Test!

Tollen's reagent

Reagents & Conditions:
Ammonical solution of AgNO3, [Ag(NH3)2]+
warm

Observations: 
aliphatic aldehyde (RCHO) ---> Silver mirror
aromatic aldehyde (C6H5CHO) ---> Silver mirror

RCHO + 2[Ag(NH3)2]+ + 3OH- ---> RCOO- + 2Ag + 4NH3 + 2H2O
Reaction: Nucleophilic Substitution

NH3 + excess RX -----> ??

reagents & conditions: ???
Reaction: Nucleophilic Substitution

NH3 + excess RX -----> (NR4)+ + HX

reagents & conditions: ethanol solvent, heat in sealed tube
Reaction: Nucleophilic Substitution

excess NH3 + RX -----> ??

reagents & conditions: ??
Reaction: Nucleophilic Substitution

excess NH3 + RX -----> RNH+ HX

reagents & conditions: ethanol solvent, heat in sealed tube
Reaction: nucleophilic add.

RCOR' + ?? -----> RCR'(OH)CN

reagents & conditions: ???
Reaction: nucleophilic add.

RCOR' + HCN -----> RCR'(OH)CN

reagents & conditions:
HCN (NaCN and dilute HCl or H2SO4)
trace amounts of NaCN/NaOH
Functional Group Test!

Carbonyl cpd (-C=O) + 2,4-dinitrophenylhydrazine

.-.-.-.-.-.-.-.-.-.-.-.-.-.

Observations: Orange precipitate
Rxn: CH3COCH3 + 2,4-DNPH  --> see next page + H2O
Functional Group Test!

Tri-iodomethane test

methyl carbonyl / CH3-CHR-OH 

reagents & conditions: ??
Observations: ??
Rxn: ??
reagents & conditions: Iodine in Aq. NaOH, WARM
Observations: yellow ppt (CHI3) with antiseptic smell
Rxn: 
RCOCH3 + 3I2 + 4OH- ---> RCOO- + CHI3 + 3I- + 3H2O
Mechanism!

Nucleophilic addition of HCN to Carbonyl compound 
Reaction: Esterification

RCOOH + R'COH -----> RCOOCR' + H2O

reagents & conditions: ???
Reaction: Esterification

RCOOH + R'COH -----> RCOOCR' + H2O

reagents & conditions: conc. H2SO4, Heat and reflux
Acidity of Organic Cpds!

Which compounds (ROH/phenol/RCOOH) react with: 
Na, NaOH, NaHCO3, Na2HCO3

Why? 
acidity : RCOOH > phenol > H2O > ROH

ROH w Na only
Phenol w Na & NaOH
RCOOH w ALL 

greater anion A- stability -> greater dissociation of HA -> greater acidic strength

Alcohol -> RO- destabilised by electron-donating R => not very stable

Phenol -> phenoxide stabilised by delocalisation of lone pairs into benzene ring

Carboxylic Acid -> carboxylate ion stabilised strongly by resonance stabilisation w 2 O atoms
Functional Group Test!

distinguish CH3OH, C6H5OH, CH3COOH

reagents & conditions: ??
Observations: ??
Rxn: ??
Functional Group Test!

distinguish CH3OH, C6H5OH, CH3COOH

reagents & conditions: Add NaHCO3/Na2HCO3

Observations: vigorous evolution of CO2 for carboxylic acid only
explain the mechanism of heterogeneous catalyst
adsorption of rectant particles onto catalyst surface. weak bonds form between reactant and catalyst

reaction at surface occurs at faster rate as reactant molecules are brought closer together & existing interactions in reactant molecules are weakened

desorption of products from catalyst surface
why are transition metal compounds (hydrated crystal/ aq. solution) coloured?

- in hydrated crystal form/ aq. sol., transition metal ions have partially filled 3d orbitals.

- the 5 degenerate 3d-orbitals of the transition metal ion are split into 2 different energy levels w a small energy gap due to the approach of ligands (d splitting)

- electrons in lower energy d-orbitals can absorb energt of s certain wavelength (E=hc/Lambda) from the visible light spectrum and be excited to the higher energy d-orbitaks (d-d transition)

- the colour of the complex is the complementary of the wavelength absorbed
Cl2 with hot aq. NaOH (70oC)

Cl2 + 6OH- ---> ???
3Cl2 + 6OH- ---> 5Cl- + ClO3- + 3H2O
Cl2 with cold aq NaOH (15oC)

Cl2 + OH- ---> ???
Cl2 + 2OH- ---> Cl- + ClO- + H2O

when warmed

3ClO- ---> 2Cl- + ClO3-
Br2(g) + H2(g) ---> 2HBr(g)

reaction conditions/reactivity: ???
reacts w H2 above 200oC and in the presence of Pt catalyst
colour of Br2 in organic solvent
reddish brown
I2 with cold aq. NaOH (15oC)

3I2 + 6OH- ---> ???
3I2 + 6OH- ---> 5I- + IO3- + 3H2O

*IO- is unstable & decomposes rapidly at 0oC
colour of Cl2 in organic solvent
colourless
All Chromies Shine except Laid Back Slackers
All Chromates (CrO42-) Soluble except Lead, Barium & Silver
Solubility of Grp II hydroxides increases down group

Why?
down the group:
cationic radius (r+) increases.

OH- radius <<< cationic radius
=> (r+ + r-) ~ r+
=> LE = k(1/r+)

as r+ increases, LE less exothermic
=> (-LE) less positive


- OH- much smaller than cation
=> ^Hhyd of OH- very exothermic compared to ^Hhyd of cation.
=> ^Hhyd(total) ~ ^Hhyd(OH-)
=>^Hhyd constant negative down grp

therefore, since ^Hsol = ^Hhyd -LE,
^Hsol is more exo down grp
=> solubility increases

colour of ppt

AgBr
colour of ppt

Cream
NaBr + H2SO4 ---> ???

HBr + H2SO4 ---> ???

observations: ???
NaBr + H2SO4 ---> HBr + NaHSO4

HBr= white fumes

HBr + H2SO4 ---> Br2 + SO2
+ 2H2O

HBr= brown fumes
SO2= colourless pungent gas
colour of Cl2 in water
yellowish green
colour of ppt

AgCrO4
colour of ppt

reddish brown

soluble in acid
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