Organic Chem Flashcards
at what conditions does a primary alcohol get dehydrated into alkene and release 1 water molecule
H2so4
170 - 180 C
product and conditions for weak dehydration of 2 primary alcohols
140 C h2so4
ether and water
what happens when we try to oxidize tertiary alcohol under extreme conditions
alcohol gets dehydrated into alkene, and is then cleaved and oxidized into 1 ketone and 1 aldehyde
what is used in sarrett’s oxidation of alcohols?
CrO3
pryidine
difference between sarrett’s and collin’s oxidation
collins also uses CH2Cl (dichloromethane) as a solvent along with cro3 and pyridine
describe jone’s oxidation of alcohol
cro3 (chromium oxide/trioxide/chromic acid)
H2SO4
and acetone is the solvent.
only one out of the 3 that further oxidizes aldehyde into carboxylic
cleavage of diols could be done w kmno4 to get carboxylic acid, could it be done with a weaker regant?
periodic acid (HIO4) gives us two aldehydes
what is the dichromate test for
detection of ethanol for drunk drivers
dichromate turns green from orange
acetalaldehyde is formed
what is the lucas test for
differentiation of tert/sec/primary alcohols
alcohol reacts with hcl under zinc chloride catalyst to give a clody/oily solution (RCL and h2o)
tert forms immediately whereas primary forms on heating
describe the results of the victor meyer’s test for the differentiation of alcohols
1 : blood red
2 : blue
3 : no color
how to synthesise ethers using williamson’s synthesis
2 steps
1. acid metal reaction bw alcohol and Na
2. React the sodium alkoxide formed RO-Na+ with R-X (alkyl halide) Sn2 to give us ether and NaX
how to syntheisise ethers using halogenoalkanes
React 2 RX with Ag2O at high temp. 2AGX form along with 1 ether
ethers react with acyl halides in the presences of …….. to give us?
ZnCl2 catalyst
RX and ester
ethers act as a nucleophile and a base to react with strong acid to produce
oxonium ion and then salt
(with hbr, h2so4)
not with HI tho, forms RI and alcohol instead
phenol when treated w conc h2so4 and then w conc hno3 give us
2,4,6 - nitrophenol
during hydration of alkenes to form alcohols, alkenes are first dissolved in?
conc h2so4
esterfication follows which reaction mechanism
nucleophillic sub
trans isomers have —- bp but —– mp
low bp due to non polar nature but high mp as they r closely packed
the type of isomerism that arises due to shifting of proton from one atom to another in the same molecule is called
tautomerism
how many organic compounds r known
over 6 million
aliphatic compounds is another name for
acyclic compounds
the wolf kishner reduction
ketone/aldehydes —-> alkane
NH2NH2
KOH alc
heat
on what basis do we determine which alkene reacts fastest w H2 under hydrogenation condition
the one w least stearic hinderance/ alkyl groups subsitituted on CC
list all the dehydrating agents
h2so4 , p2o3, p4o10, h3po4, al2o3
order of reactivity of alk to give electrophillic addition reactions
alkene>akyne> alkane
how could we produce is cis alkene from an alkyne
hydrogenation reaction
H2 and lindlar pd- poisoned catalyst (pt catalyst would further reduce it to alkane)
how could we produce a trans alkene from an alkyne
Na and NH3
Na breaks 1 pi bond and donate one electron to one C, forming a radical ion and a carboanion
The H goes to the anion and the radical further forms an anion from sodium metal and also accepts H from nh3
list electron withdrawing groups which deactivate the benzene ring, making it less reactive
- carbonyl groups CHO,
· halogens (F, Cl);
· nitriles CN;
· nitro groups NO2.
list electron donating groups which activate the ring
· alkyl groups;
· alcohol groups;
· amino groups.
aromic compounds burn with yellow sooty flame because
they have high percentage of carbon
incomplete combustion
why are alkenes more reactive than benzene w.r.t electrophillic sub
Benzene has a cyclic structure with delocalised electrons and with more resonating structures which make it more stable. As it is more stable so it is less reactive.
order of reactiivty of alkenes with hydrogen halides is
HI>HBr>HCl>HF
ethanenitrile can be converted into ethanoic through ——– intermediate
acetamide
the formation of acetic ahnydride from acetic acid follows the mechanism
SN
molar mass of formic acid in benzene comes out to be
92
nitrobenzene is reduced to phenylamine (aniline) by
Sn/HCL
phenylamine + CH3Cl + 3KOH —>
phenyl isocyanide C6H5CN + 3KCL +3H2O
the primary secondary and tertiary amines can be distinguised by
hinsberg’s reagent C6H5SO2Cl
1 : alkali soluble benzene sulphonamide
2 : insoluble version of 1
3 does not react
what is the hoffman bromoamide reaction/ degradation reaction
when primary amine reacts w Br and NaOH then one carbon less primary amine will form
the leaving group in SN2 reaction is
a good leaving group is a weak base
what is a good leaving group
a small negatively charged ion that can easily leave a molecule without causing much disruption (hso4- and br-). OH- is a bad leaving group because its a strong nucleophile and has high charge to size ratio so very attracted to carbon
in a reaction havig both alkyl halide and base the base will attack on —-?
beta hydrogen
what is cannizaro reaction
carbonyl compound reacts with naoh or koh to form one cooh (oxidized) and alcohol (reduced)
oxidation will occur on carbon w less stearic hinderance(bulky groups) and electron withdrawing groups.
on dry distillation of calcium methanoate, what is produced
acetaldehyde (ethanal ) and CO2
carbonyl compounds undergo nucleophillic addition because
electronegativity difference and pi bond
FeCl3 is used to differentiate
phenols : purple
alcahols : colorless
what is clemenson reduction
carbonyl group is reduced to CH2 when treated with amalgamated zinc and conc hcl
when acetylene is passed thru hot iron tube at 400 C it gives
benzene
non polar product is formed in what type of reaction (E or S)
Elimination
a better leaving group has following characteristics
- stable anion
- large sized
- favors sn1 instead of sn2
formation of phenols in dow’s method is
aromatic nucleophilic sub of chlorobenzene to phenol
most acidic alcohol
methanol
which gives positive iodoform test
ethanol and 2-alcohol
and methyl ketones
phenol reacts with acyl halide to give
aromatic ester
what reacts w NaHSO3 to give white ppt?
aldehydes and small methyl ketones
oximes are formed upon reaction of aldehydes or ketones with
hydroxyl amine
acetone can be prepared by dry distillation of?
calcium acetate
Aldehydes or ketones possessing alpha hydrogen undergo?
aldol condensaition
those that dont : unergo cannizaro reaction
Carboxylic acids can be prepared from oxidation of ketones by
pop off rule 🍑
