1. What is nitration of an aromatic compound representative of? What kind of reaction?

electrophilic aromatic substitution

2. If there is an EWG on the aromatic, what is the product?

meta

3. If there as an EDG on the aromatic, what is the product?

ortho/para

4. What is the underlying reason why EDG--> o/p and EWG --> meta?

resonance: EDG, once the electrophile has been added, there can be a positive charge on three places on the ring, and on the EDG, while if the electrophile was meta on an EDG, there wouldn't be as much resonance and stability; EWG , there can be resonance on three places on the ring in the meta position, but if the electrophile is ortho or para when there is an EWG, there can only be two resonance structures because you cannot have a positive charge on the carbon connecting to the EWG

5. Why is a catalyst used in these reactions?

generate a very strong electrophilic species which could react with very non-reactive aromatic C=C bonds

6. How do you synthetically make a NO2+ group to add to a ring?

mixing H2SO4 and HNO3

7. Which of these two acts as the acid and which as the base? Why?

H2SO4 acts as the acid and HNO3 acts as the base due to relative acidity

8. What would be the role of a nail in a reaction of bromination of toluene?

acts as a catalyst

9. What would happen if the nail was old?

slower reaction because the nail is oxidized

10. What conditions would you need to use to introduce Br onto the carbon of the methyl group of toluene?

UV light (free-radical halogenation)

11. Why is the 1,4 product of nitration of bromobenzene usually formed rather than 1,2?

steric hinderance (NO2 group is big)

12. What is more polar--4 or 2 bomonitrobenzene? How can you tell this?

4 moves faster on a polar silica gel, therefore less polar
2 moves slower, therefore more polar

13. How to calculate Rf values:

distance travelled by spot/solvent front

14. How to calculate percent yields of reactions:

find moles of starting materials, less moles = limiting reactant, then do a mole ratio (based on the overall reaction) of limiting reactant to product and that is the number of moles of theoretical product (can then be changed to grams)

then, actual is your actual findings

% yield = actual/theoretical x 100

15. What are the possible side reactions of nitration of bromobenzene?

dinitration-can occur at ortho, para or at both ortho positions; occurs in overheating
meta product- happens very rarely becuase bromine is an ortho/para director