Organic Chemistry 14

Chemistry Level 4

An Unsaturated hydrocarbon (X) contains 6 carbon atoms . On

reductive Ozonolysis it forms two moles of ethanal and one mole of

glyoxal . When X is treated with Acidified Potassium permanganate ,

a colourless solution is obtained.

How Many 1,2-addition product(s) is/are possible when compound(X)

is treated Hydrochloric Acid In presense of carbon tetrachloride?

Consider Major and minor products as well as there stereoisomers.

Asked in my test


The answer is 8.

Prakhar Bindal by Prakhar Bindal , 22, India

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2 solutions

From the given information , the compound X is Hexa- 2 , 4 2,4 -diene. Now, coming to the question , we are only required to find the no. of 1 , 2 1,2 products. By electrophilic addition , a Cl atom can add at either of two positions of a double bond (as we are asked to include major as well as minor products) and the configuration so generated at that centre will be either R or S . Now, corresponding to each configuration of the newly generated chiral centre there are two configurations (cis or trans) of the other (untouched or unreacted) double bond . Hence, the answer is 2 ∗ 2 ∗ 2 = 8 2*2*2=8

1 Helpful 0 Interesting 0 Brilliant 0 Confused
Aryan Mehra
Apr 15, 2017

Adding chlorine at 1,2 position will give a chiral entre and so countvthat product as 2 in number because stereoisomers are to be invluded. Then perform the addition on both the double bonds to get a tetra chloride. This product has 2 cjiral centres and will hive 4 products. Similarly perform a 1, 4 addition to get a geometrical isomer profuct with count 2. Hence the answer is 2+4+2=8.

Hope it helps

0 Helpful 0 Interesting 0 Brilliant 0 Confused

Well this isn't the correct solution . you got it luckily :p .

Read the question it says How many 1,2 addition products are possible. you need to only count 1,2 addition products. Moreover in case of 1,2 addition chlorine can add to either of two positions (I Never said major product) . Each of them will have 2 stereogenic centres one double bond and one chiral centre . hence we get 4 products in each of two cases making total of 8 products

Prakhar Bindal - 4 years, 2 months ago

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