Which intermediate is formed when acetyl chloride reacts with benzene in the presence of AlCl₃?
AAcetyl cation (CH₃CO⁺)
BPhenyl carbocation
CChlorobenzene adduct
DAluminum-chlorine complex
Correct Answer:
A. Acetyl cation (CH₃CO⁺)
EXPLANATION
In Friedel-Crafts acylation, AlCl₃ facilitates the formation of the acetyl cation (CH₃CO⁺) from acetyl chloride. This electrophilic acylium ion then attacks the benzene ring.
In the bromination of toluene, the ortho:para ratio is approximately 2:1 instead of 1:1 due to:
ASteric hindrance at ortho position
BThermodynamic stability of para isomer
CKinetic control with partial steric effects
DElectronic effects favoring para position
Correct Answer:
C. Kinetic control with partial steric effects
EXPLANATION
Although para is thermodynamically more stable, ortho is kinetically favored but sterically hindered. The 2:1 ratio reflects kinetic control with steric factors reducing ortho product.
The enolate ion formed from a ketone in basic conditions attacks an alkyl halide in the:
ACarbon atom (α-position)
BOxygen atom
CThrough radical mechanism
DThrough concerted mechanism
Correct Answer:
A. Carbon atom (α-position)
EXPLANATION
Although the enolate has negative charge on both oxygen and carbon (resonance), the carbon is more nucleophilic toward alkyl halides. The SN2 attack occurs at the alkyl halide carbon, not the enolate O.
In the Robinson annulation reaction, the product formed is:
AAn aromatic compound
BA bicyclic ketone
CA linear diene
DA carboxylic acid
Correct Answer:
B. A bicyclic ketone
EXPLANATION
The Robinson annulation combines a Michael addition followed by an aldol condensation, forming a bicyclic ketone product with a new six-membered ring fused to an existing ring system.
The directing effect of the amino group (-NH2) in electrophilic aromatic substitution is:
ADeactivating, meta-directing
BDeactivating, ortho/para-directing
CActivating, ortho/para-directing
DActivating, meta-directing
Correct Answer:
C. Activating, ortho/para-directing
EXPLANATION
The amino group is a strong electron-donating group (by resonance) that activates the benzene ring and directs incoming electrophiles to ortho/para positions due to resonance stabilization of the intermediate.
When propyne undergoes hydration in the presence of Hg2+/H2SO4, the major product is:
APropanol
BPropanal
CAcetone
DPropanoic acid
Correct Answer:
C. Acetone
EXPLANATION
Propyne (CH3C≡CH) hydrates to form an unstable enol intermediate. The enol tautomerizes to acetone (CH3COCH3), following Markovnikov's rule with H adding to the carbon with more H atoms.
The mechanism of the esterification reaction between a carboxylic acid and alcohol is:
ASN1 mechanism
BSN2 mechanism
CNucleophilic acyl substitution via tetrahedral intermediate
DElimination-addition
Correct Answer:
C. Nucleophilic acyl substitution via tetrahedral intermediate
EXPLANATION
Esterification follows the nucleophilic acyl substitution mechanism: the OH of the alcohol attacks the carbonyl carbon after protonation, forming a tetrahedral intermediate that collapses to form the ester.