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.
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Chapter 16 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
- Substance X is known to exist at 1 atm in the solid, liquid, or vapor phase, depending on the temperature. Additionally, the values of these other properties of X have been determined: melting point enthalpy of fusion 90. °C 8.00 kJ/mol boiling point 130. °C enthalpy of vaporization 44.00 kJ/mol density 2.80 g/cm³ (solid) 36. J.K mol (solid) 2.50 g/mL (liquid) heat capacity 32. J.Kmol (liquid) 48. J.Kmol (vapor) You may also assume X behaves as an ideal gas in the vapor phase. Ex Suppose a small sample of X at 50 °C is put into an evacuated flask and heated at a constant rate until 15.0 kJ/mol of heat has been added to the sample. Graph the temperature of the sample that would be observed during this experiment. o0o 150- 140 130- 120- 110- 100- G Ar ?arrow_forwardMechanism. Provide the mechanism for the reaction below. You must include all arrows, intermediates, and formal charges. If drawing a Sigma complex, draw all major resonance forms. The ChemDraw template of this document is available on Carmen. Br FeBr3 Brarrow_forwardCheck the box under each compound that exists as a pair of mirror-image twins. If none of them do, check the none of the above box under the table. CH3 OH CH3 CH2 -CH-CH3 CH3 OH OH CH-CH2-CH- -CH3 CH3 CH3 OH OH CH3 C -CH2- C. -CH3 CH3- -CH2- -CH-CH2-OH OH CH3 none of the above كarrow_forward
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- How many different molecules are drawn below?arrow_forwardWith the reference to a anion A, Label compounds B-F as an isomer or resonance strcuture of A. FOr each isomer indicate what bonds differs from A. Provide steps and undertanding on how you come up with work.arrow_forwardProvide steps and also tips to undertand how to do on my own. Add the correct number of hydrogen atoms for each carbon atom and lone pairs to each oxygen atom.arrow_forward
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