d) Explain how the haloform reaction can be used to distinguish between butan-2-one and propanal....

Question

d) Explain how the haloform reaction can be used to distinguish between butan-2-one and propanal. Include a reaction mechanism for any reaction which occurs. If you have photographs of the iodoform experiment you may wish to include these.d) Compounds having CH3CO- group or produces CH3CO- group after oxidation, responds to haloform reaction.The propanal does not have a chloromethyl group whereas the ketone, butan-2-one has one chloromethyl group. So, The latter undergoes a haloform reaction whereas the former does not.
	
Document Preview: Sharon Assignment Resubmission:Please correct the following?For one of the Esters below write a balanced equation and mechanism?Sample numberAcetic AcidFormic AcidBenzoic Acid2-hydroxy benzoic acid1EthanolNail varnish remover. Ethyl acetateVery effervescing. Thinners. Ethyl MethanoteGermoline smell. Ethyl benzoateNitrates. Ethyl hydroxyl benzoic acid2Propan-1-olFruity. Propyl AcetateNail polish remover PropylmethanateClover. Propyl benzanateFruity. Propyl hydroxyl benzoic acid.3Butan-1-olPear Drops. Bytyl acetateWeak pear drops. Butyl methanoatePineapple. Butyl benzoateButyl hydroxyl benzoic acid.4MethanolNail polish remover. Methyl acetateNo Smell. MethonoateDeep Heat.Methyl benzoateDeep heat. Methyl benzoated) Explain how the haloform reaction can be used to distinguish between butan-2-one and propanal.  Include a reaction mechanism for any reaction which occurs.  If you have photographs of the iodoform experiment you may wish to include these.d) Compounds having CH3CO-  group or produces CH3CO-  group after oxidation, responds to haloform reaction.The propanal does not have a chloromethyl group whereas the ketone, butan-2-one has one chloromethyl group. So, The latter undergoes a haloform reaction whereas the former does not.A compound containing a chloromethyl group is treated with a halogen in alkaline solution – polyhalogenation of a-hydrogens takes place. A haloform along with a carboxylate anion are produced.Mechanism:Step1: Hydroxide ion abstract acidic proton from the ketomethyl group and produce an enolate.Step2: The enolate reacts with iodine to produce a halogenated ketone and iodide ionStep 3 & 4:  Step 1 and step 2 are repeated to produce trihalogenated ketone:Step 5: Hydroxide ion attacks carbonyl carbon and free CI3- which is a good leaving group because of the stability imparted by three halogen atoms.You started with Iodine ???????????? You have mixed up using Iodine with chlorine in the...

Robert · Accepted Answer

1) Ester formation mechanism for ethanol and acetic acid:
HO
ethanol
O
HO
acetic acid
+
H
+
O
O
+ H2O
mechanism:
O
HO
acetic acid
H
+
O
HO
H
O
ethanol
H
O
O
HO
H
H
+
O
O
H2O
H
O
O
H2O +
-H
+

2) Iodoform mechanism:

d) Explain how the haloform reaction can be used to distinguish between butan-2-one and propanal. Include a reaction mechanism for any reaction which occurs. If you have photographs of the iodoform...

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