a)
Interpretation:
Draw the products obtained when the compound shown (methoxybenzene) reacts with (i) Br2, FeBr3 and (2) CH3COCl, AlCl3.
Concept introduction:
Aromatic rings can be brominated using Br2 in the presence of FeBr3. The electrophile is Br+. Friedal-Crafts acylation reaction occurs when an
To draw:
The products obtained when the compound shown (methoxybenzene) reacts with (i) Br2, FeBr3 and (2) CH3COCl, AlCl3.
Answer to Problem 24VC
(i) The products obtained when the compound shown (methoxybenzene) reacts with Br2/FeBr3 are p-bromomethoxybenzene and o-bromomethoxybenzene.
(ii) The products obtained when the compound shown (methoxybenzene) reacts with CH3COCl/AlCl3 are p-acetylmethoxybenzene and o-acetylmethoxybenzene.
Explanation of Solution
The methoxy group attached to the benzene ring is an ortho & para directing group. When methoxybenzene is brominated and alkylated it directs the incoming electrophiles, Br+ and CH3CO+ to ortho & para positions.
(i) The products obtained when the compound shown (methoxybenzene) reacts with Br2/FeBr3 are p-bromomethoxybenzene and o-bromomethoxybenzene.
(ii) The products obtained when the compound shown (methoxybenzene) reacts with CH3COCl/AlCl3 are p-acetylmethoxybenzene and o-acetylmethoxybenzene.
b)
Interpretation:
Draw the structures of the products obtained when the compound shown, p-methylbenzaldehyde reacts with (i) Br2, FeBr3 and (2) CH3COCl, AlCl3.
Concept introduction:
Electrophilic substitution of disubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.
To show:
The major product(s) produced when p-methylbenzaldehyde reacts with (i) Br2, FeBr3 and (2) CH3COCl, AlCl3.
Answer to Problem 24VC
(i) The major product produced when p-methylbenzaldehyde reacts with Br2/FeBr3 is 3-bromo-4-methylbenzaldehyde.
(ii) The major product produced when p-methylbenzaldehyde reacts with CH3COCl/AlCl3 is 3-acetyl-4-methylbenzaldehyde.
Explanation of Solution
The
(i) The major product produced when p-methylbenzaldehyde reacts with Br2/FeBr3 is 3-bromo-4-methylbenzaldehyde.
(ii)The major product produced when p-methylbenzaldehyde reacts with CH3COCl/AlCl3 is 3-acetyl-4-methylbenzaldehyde.
Want to see more full solutions like this?
Chapter 16 Solutions
Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
- For the following synthetic scheme, draw the structure of the product of each reaction. Ignore stereochemistry for all structures.arrow_forwardWith this in mind, draw the product when each compound undergoes anintramolecular Diels–Alder reactionarrow_forwardRank the following in order from slowest to fastest rate of reaction in a Diels–Alder reaction with buta-1,3-dienearrow_forward
- Explain why methyl vinyl ether (CH2 = CHOCH3) is not a reactive dienophile in the Diels–Alder reaction.arrow_forwardRank the following compounds in order from slowest to fastest rate of reaction in a Diels–Alder reaction with ethene.arrow_forwardWhich solvents favor SN1 reactions and which favor SN2 reactions?arrow_forward
- The molecule in the box is the product of a diels alder reaction. Which of these is the dienophile in that reaction ? A B C D or E?arrow_forwarda. Which of the following compounds cannot be prepared by a Heck reaction?b. For those compounds that can be prepared by a Heck reaction, what starting materials are required?arrow_forwardFor each pair of compounds, a state which compound is the better SN2 substrate. (a) cyclohexyl bromide or 1-bromo-1-methylcyclohexanearrow_forward
- Two of the following will give the same dimethylcyclooctatriene prod (A) while the third one will give the different dimethylcyclooctatriene (B) Preditc which of the ffg gives prod A or Barrow_forwardDraw the major organic product of the reaction. Ignore stereochemistryarrow_forwardHow Reactivity Depends on the Basicity of the Leaving Group?arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning