Identifying an Organic Compound

Chemistry Level 4

Let the molecular formula of the compound be $\ce{C_x H_y O_z}$ .
The following observations were made on the sample

The compound gave Red colour with Ceric Ammonium Nitrate .
The compound gave Iodoform test.
The compound reacted with 3 moles of Grignard Reagent .
The compound reacted with $\ce{NaHCO3}$ and evolved $\ce{CO2}$ gas.
The compound reactes with 2,4-DNP.
The compound has no branched chain and has IHD value equal to 2.
On heating, it gave $\alpha, \beta$ unsaturated Carboxylic acid (with other functional groups also there ).
The compound is found to have $( 2z - 1 )$ Carbon atoms

Enter your answer as $x × y × z × n$ , where n denotes the number of functional groups present in the compound.

The following functional groups may be present

$\ce{-COOR , -COOH , epoxy , -OH , -C=O , -CHO}$ .

Original

1 solution

Neelesh Vij
Aug 21, 2016

Decoding each statement:

1) Red colour with cerric ammonium nitrate means presence of alcohol.

2) iodoform test means compound has $\ce{-CO - CH_3}$ group at the end

3) currently of no help ;P

4) Reaction with $\ce{NaHCO_3}$ means presence of $\ce{COOH}$ group

5) As compound has a keto group (iodoform test) so it can $\ce{2,4 DNP test}$

6) Indicating no double bonds (as there are in $\ce{CO}$ and $\ce{COOH}$

7) Shows the position of alcoholic group i.e on beta carbon to $\ce{COOH}$ group

8) to find number of carbons , as there are 4 oxygen atoms so there are 7 carbon atoms

Finally drawing picture of compound:

$\ce{HOOC-CH_2-CH(OH) -CH_2 -CH_2 -C(O) -CH_3}$

which satisfies point no. 3

C=7 H=14 O=4 Funct=3 So ans must be 1176

aryan goyat - 4 years, 7 months ago

Sorry mai pagal hu H galat gin leye

aryan goyat - 4 years, 7 months ago

Ohh!.. that happens with me too :P

Prakhar Bindal - 4 years, 7 months ago

with me too :P

Md Zuhair - 2 years, 1 month ago