The problem statement: PART 1: i. The bottle(s) that could contain a strong acti

Question

The problem statement:

PART 1:

i.

The bottle(s) that could contain a strong activating group are:
a) Bottle E

b) All the bottles except E

c) Bottles E and B

d) Bottles E and F

e) All the bottles could

ii.

Which bottle(s) could contain a benzene derivative that has an acidic C-H bond?
a) Bottles A and B

b) Bottles A and D

c) Bottles A and E

d) Bottle A

e) None of the bottles could

iii.

Which bottle(s) could contain an electron withdrawing group?
a) Bottles B and C

b) Bottles A and B

c) Bottles E and D

d) Bottle F only

e) Bottle D only

iv.

Which bottles are likely to contain a halogenated benzene derivative?
a) Bottles A, C and E

b) Bottles C and F

c) Bottles C, D and F

d) Bottles A, C and F

e) Bottles A and F

v.

Which of the following bottles could contain a carbonyl?
a) Bottle A

b) Bottle F

c) Bottle E

d) Bottle B

e) Bottle C

vi.

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

PART 2:

During the clean-up some of the labels were recovered: 3-bromoacetophenone, benzene, toluene, chlorobenzene, nitrobenzene and aniline.

i.

Which of the following labels would be correct?
a) Bottle A could contain toluene

b) Bottle D could contain toluene

c) Bottle A could contain benzene

d) Bottle F could contain toluene

e) None of the bottles could contain toluene

ii.

Which of the following bottles could contain nitrobenzene?
a) Bottle C

b) Bottle D

c) Bottle E

d) Bottles B and D

e) Bottles A

iii.

Which chemical is most likely to be in bottle F?
a) Benzene

b) Toluene

c) Nitrobenzene

d) Aniline

e) Bromoacetophenone

iv.

A sample from bottles E and F were combined with a small amount of p-toluenesulfonic acid. The product from this reaction would contain:
a) An amide

b) An amine

c) An imine

d) A hemiaminal

e) No reaction would occur

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: | Bottle C | Bottle D 1 Bottle F | Bottle B Bottle E Bottle A Br2 (excess) No reaction No reaction No reaction No reaction Spontaneous No reaction reaction occurred Fast Cl2+ FeCls Multiple A single M Multiple Slow Multiple products product formed productsreaction but reaction. products formed multiple Multiple formed formed products products did eventually form formed No reaction No reaction No reaction Multiple No reaction New product observed products formed Acetyl Multiple A single Multiple No reaction Multiple Multiple chloride products product products Alcl products formed products formed formedformed formed KOH, Pd, No reaction No reaction A single No reaction No reaction New product formed PR product KOH, H2O No reaction No reaction A single observed No reaction No reaction2 products product formed formed Meli, THFNo reaction followed by acidic work No reaction No reaction No reaction No reaction New product observed KOM, EtOH New No reaction No reaction No reaction Multiple New followed by product Mel products formed product observed observed DOLL

Explanation / Answer

1) The bottle(s) that could contain a strong activating group is E and F because in E and F bottles only multiple products were observed which is only due to reaction occur in presence of strong activating groups.

2) The bottle(s) that contain a benzene derivative which has an acidic C-H bond are Bottles A and B because Cl2+FeCl3 and Acetyl chloride + AlCl3 will easily remove acidic C-H bond from benzene derivative and install Cl and acetyl group on them respectively. (Electrophilic Aromatic Substitution halogenation)

3) The bottle contains an electron withdrawing group could be Bottle D since there is almost no reagent which is giving some new spots. The reason is that electron withdrawing group deactivates the ring which makes it hard to react with any intermediates.

4) The bottles likely to contain a halogenated benzene derivative could be Bottles C and F because KOH, Pd, PR3 will remove halogen from benzene and install an alcohol group.

Related Questions

Navigate

• Browse (All)
• Browse T
• Subjects

---

---

Integrity-first tutoring: explanations and feedback only — we do not complete graded work. Learn more.