Question 29 a.) ?ANSWER THE FOLLOWING BASED ON THE GIVEN DATA BELOW: An unfortun

Question

Question 29 a.)

?ANSWER THE FOLLOWING BASED ON THE GIVEN DATA BELOW:

An unfortunate plumbing incident in a chemical storage facility resulted in the labels of several bottles were washed off. These bottles were from the benzene shelf but not much else is known about the contents. An intern was tasked with determining what each bottle contained by performing a series of reactions with a small sample from each bottle. The results they obtained is compiled in Table 1 below:

i.)

Which of the following bottles could contain a carbonyl?

a) Bottle A

b) Bottle F

c) Bottle E

d) Bottle B

e) Bottle C

ii.)

There is potential for benzyne chemistry with whatever is in bottle(s):

a) Bottle B

b) Bottles C and F

c) Bottle C

d) Bottle F

e) None of these bottles

D L Bottle A Bottle B Bottle C Bottle D Bottle E Bottle F Brz (excess) No reaction No reaction No reaction No reaction Spontaneous No reaction reaction occurred Cl2 + FeCl3 Multiple A single Multiple Slow Fast Multiple products product products reaction but reaction. products formed formed formed multiple Multiple formed products products did formed eventually form Br + hv New No reaction | No reaction | No reaction | Multiple No reaction product products observed formed Acetyl Multiple A single Multiple | No reaction | Multiple Multiple chloride + products product products products products AlCl3 formed formed formed formed formed KOH, Pd, No reaction. No reaction A single No reaction No reaction New product product formed observed | KOH, H2O | No reaction | No reaction | A single No reaction No reaction 2 products product formed formed MeLi, THE No reaction No reaction No reaction No reaction No reaction New followed by product acidic work observed PR3 up KOH, EtOH New followed by product Mel observed No reaction | No reaction | No reaction | Multiple products formed New product observed

Explanation / Answer

ANSWER:

(I) Bottle F coud contain a carbonyl group. The carbonyl group may be a bezyl carbonyl group e.g benzaldehyde, since the bottles were from benzene shelf. Bottle F reacts with Cl2+ FeCl3 to form multiple products, this may be due to the benzene group. It reacts with KOH, H2O to form two products. This may be due to Cannazaro's reaction of benzaldehyde to form two products upon disproportionation. It react wih MeLi in THF to form new product, the product may be methylation product of the benzaldehyde.

(II) Bottle C has the potential for benzyne chemistry.

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