JEE Alcohols, Phenols and Ethers

carbinol

CH3OH

chloral hydrate

(stable)

action of Alk KMnO4 on 3⁰ alkane

3⁰ alcohol formed

Hydroboration reaction

hydroboration oxidation forms _____ product(mark/antimark)

antimark

oxymercuration/demercuration forms

alcohols

hydroboration oxidation forms

alcohols

oxymercuration/demercuration reaction

oxymerc/demerc reaction gives ___ product(markovnikov/antimark)

markovnikov

difference between products of hydroboration oxidation and oxymercuration/demercuration

Hydroboration forms antimark product, Oxymerc forms markovnikov product

Zn/HCl, Na/ethyl alc., LiAlH4 and NaBH4 are reducing agents. Which of the following cannot reduce =? What is the exceptional case where it can?

1) LiAlH4, NaBH4
2) LiAlH4 - when phenyl group is present at beta position

NaBH4 does not affect ___ in reduction

C=C, N=N, -COOH, ester, -CN-, NO

difference between action of HNO2/NaNO2/HCl on aniline and R-NH2

aniline - forms diazo salt(stable)
R-NH2 - forms diazonium ion, then alcohol

hydrolysis of ester yields

carboxylic acid + alcohol

which bond is cleaved in hydrolysis of ester?

C-O bond(not C=O bond)

invertase converts

glucose to fructose(GIF)

zymase converts

glucose + fructose to ethyl alcohol

diastase converts

starch to maltose

maltase converts

maltose to glucose

enzymes used in formation of ethyl alc from molasses

invertase, zymase

enzymes used in formation of ethyl alcohol from starch

diastase, maltase, invertase, zymase

Reactivity of alcohols where cleavage of O-H takes place is of order

primary > secondary > tertiary

reactivity of alcohols where cleavage of C-O takes place

tertiary > secondary > primary

order of acidity of alcohols

primary > secondary > tertiary

alcohols are ___ acids(strong/weak)

weak

ease of dehydration of alcohols is of order

tertiary > secondary > primary

action of H2SO4 on C2H5 - OH

at 140°C - ether formed
at 180°C - alkene formed

action of Cu on R-CH2-OH

R-CHO

action of CAN on R-CH2-OH

R-CHO

MnO2 is used to oxidize ___ alcohols

benzylic, allylic

Action of Al(OCMe)3/CH3-O-CH3 on alcohols(R-CH2-OH)

R-CO-R + CH3-CH(OH)-CH3

Jones reagent

CrO3

action of CrO3 on alcohols

- primary alcohols converted to -COOH
- secondary alcohols converted to ketones

name the reagents that can replace CrO3 in Jone's reaction

KMnO4, Acid Dichromate, Aq Chromic acid, Collin's reagent, PDC/CH2Cl2

action of PDC/CH2Cl2 on alcohol

- primary alcohols converted to -COOH
- secondary alcohols converted to ketones

action of DMS/(COCl)2 on alcohols

- primary alcohols converted to -COOH + pyridine
- secondary alcohols converted to ketones

Haloform test comes positive for

2 degree alcohol, acetaldehyde, ethyl alcohol, methyl keto group

ROH + HClO4 is a test for alcohol. What is the colour of precipitate?

blue green, opaque

catalytic dehydrogenation of 3 degree alcohol gives

alkene

catalytic dehydrogenation of primary alcohol gives

aldehyde

catalytic dehydrogenation of secondary alcohol gives a

ketone

in Victor Meyer test, red colour indicates

1 degree alcohol

in Victor Meyer test, blue colour indicates

2 degree alcohol

in Victor Meyer test, colourless solution indicates

3 degree alcohol

___ synthesis forms ethers

Williamson

what is the combination of reagents for best yield for Williamson's synthesis

primary alkyl halide + 3 degree alkoxide

can Ph-O-Ph be formed using Williamson's synthesis?

no(if both R and R' are phenyl, tertiary, or vinyl then williamson's synthesis won't occur)

Can Ph-X + CH3-ONa be used for williamson's synthesis

phenyl group on halide cannot be used for Williamson's synthesis(Good yield is for primary alkyl halide and tertiary alkoxide)

Alkoxy-Mercuration Demercuration

difference between oxymerc/demerc and alkoxymerc/demercuration

oxymerc/demerc uses H2O, and gives alcohol
alkoxymerc/demerc uses ROH, and gives ether

Ether + H2SO4

alcohol(bond cleavage of ether)

ether + HI

alcohol and alkyl iodide(C2H5-O-C2H5 + conc. H2SO4 ----> C2H5I + C2H5OH, 2 moles of I gives 2C2H5I)

Ph-O-R + HX --->

RX + Ph-OH

ether + CO

ester

C2H5-O-C2H5 +Cl2 --->
(1) in the dark
(2) in the presence of light

(1) CH2(Cl)-CH(Cl)-O-CH(Cl)-CH2(Cl)
(2) C2Cl5-O-C2Cl5

C2H5-O-C2H5 + O2 --->(in BF3/150°C)

C2H5 - O - O - C2H5(ethyl propionate)

Dow's reaction gives ___ product

phenol

preparing phenol from Ph-SO3H

Ph-SO3H + NaOH -> Ph-ONa + HCl -> Ph-OH

Benzene + CH2=CH-CH3 (H3PO4) --->

Cumene, which on oxidation gives phenol

Dalkin reaction acts on

o- or p- hydroxyaldehyde or o- or p- aminoaldehyde

action of H2O2 + NaOH on o- or p- hydroxyaldehyde

catechol

Dakin reactions results in

catechol

which are more acidic? Phenols or Alcohols? State why.

Phenols, due to high stability of Phenoxide ion

order of stability of
1) phenol
2) m-cresol
3) p-cresol
4) o cresol
5) m nitrophenol
6) p- nitrophenol
7) o-nitrophenol
8) 3, 5- dinitrophenol
9) picric acid

picric acid> 3,5-dinitrophenol > p-nitrophenol > o - nitrophenol > m-nitrophenol > phenol > m-cresol > p-cresol > o-cresol

Schotten Bauman esterification

Ph-OH + RCOOH ---> Ph-O-CO-R + H2O

Ph-OH + RCOCl in pyridine gives

Ph-O-CO-R + HCl

acetylation of Salicylic acid gives

aspirin

reaction for preparation of aspirin

acetyl salicylic acid is also known as

aspirin

order of melting point for o-nitrophenol, p-nitrophenol and m-nitrophenol

p-nitrophenol>m-nitrophenol>o-nitrophenol (p nitrophenol has intermolecular hydrogen bonding, m does too, but o nitrophenol has intramolecular hydrogen bonding, which restricts its intermolecular hydrogen bonding)

Phenol + conc. HNO3

picric acid

Phenol + Br2 in CS2

o-bromo phenol + p bromo phenol

Phenol + Br2 in H2O

2, 4, 6 tribromo phenol

Kolbe's reaction product

salicylic acid

Kolbe's reaction reagents

NaOH, CO2, H2SO4

Kolbe's reaction

Riemer Tiemann reaction forms

o-hydroxy benzaldehyde

Riemer Tiemann reaction

Riemer Tiemann reaction intermediate

:CCl2

if ortho position is occupied, Riemer Tiemann reaction product is

para - hydroxy benzaldehyde

if Potassium phenoxide is used instead of Sodium Phenoxide in Kolbe's reaction, what happens?

Para isomer of salicylic acid is formde

action of K2S2O7 on phenol

Elb's persulphate reaction

In libermann nitroso reaction, product formed is

Order of colours observed in Libermann nitroso reaction

blue green, to red, to deep blue

compound that gives deep blue colour in Libermann nitroso reaction

(K can be replaced with Na)

diazonium salt + phenol

(the -N=N- attaches itself at para or ortho position(if para not available) of -OH group)

action of Zn dust on phenol

forms benzene

action of chromic acid on phenol

forms benzoquinone

give an example of Fries rearrangement