1. The two compounds below were targeted for synthesis to further test the conce

Question

1. The two compounds below were targeted for synthesis to further test the concept of aromaticity. What do you expect them to be? (hint: first decide how many lone pairs are on each atom)

A. both aromatic                                

B. both non-aromatic                

C. both antiaromatic   

D. 1 is aromatic, 2 antiaromatic                     

E. 1 is antiaromatic, 2 aromatic

2. One isomer of dibromoaniline is 2,3-dibromoaniline. How many isomeric dibromoaniline are there?

A)        3

B)        4

C)        5

D)        6

E)        more than 6

3. Which of the compounds listed below would you expect to give the greatest amount of meta-product when subjected to ring bromination?

A)        I

B)        II

C)        III

D)        IV

E)        V

Explanation / Answer

1. Answer is A

compound 1 is pyrylium ion which is isostructural with benzene.

compound 2 is borazine which is isostructural with benzene. Each nitrogen donates two electrons to borazine's pi cloud. boron does not donate any, but it has an empty p orbital available through which the electrons can delocalise.

2. Answer is C.

the isomers will be : 2,3-dibromoaniline, 2,4-dibromoaniline, 2,5-dibromoaniline, 2,6-dibromoaniline, 3,4-dibromoaniline, 3,5-dibromoaniline

3. Answer is B

the -COOH group is meta directing and ring deactivating in nature. a deactivating group deactivates all the positions in the ring, even the positions meta to it. it directs meta simply because it deactivates the ortho and para positions even more than it does the meta.

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