1. Which of the following compounds shows aromatic character?

A. Cyclobutadiene
B. Cyclooctatetraene
C. Cyclopentadienyl anion
D. Cycloheptatrienyl cation

Answer: C. Cyclopentadienyl anion

Explanation: It follows Hückel’s rule (4n + 2 π electrons; n = 1) and is planar and fully
conjugated.

2. In the reaction of an alkene with BH3 followed by H2O2/NaOH, the product

is:

A. Alcohol via Markovnikov addition

B. Alcohol via anti-Markovnikov addition
C. Ether
D. Aldehyde

Answer: B. Alcohol via anti-Markovnikov addition

Explanation: Hydroboration-oxidation of alkenes gives alcohols with anti-Markovnikov
regioselectivity.

3. Which of the following is most reactive towards nucleophilic aromatic

substitution?

A. Chlorobenzene
B. 2,4-Dinitrochlorobenzene
C. Fluorobenzene
D. Bromobenzene

Answer: B. 2,4-Dinitrochlorobenzene
Explanation: Electron-withdrawing nitro groups stabilize the intermediate anion and enhance
reactivity.

4. What is the product of the Hofmann rearrangement of benzamide?

A. Benzene
B. Aniline
C. Benzylamine
D. Phenyl isocyanate

Answer: B. Aniline
Explanation: Hofmann rearrangement of a primary amide gives a primary amine with one
carbon less.

5. Which of the following carbanions is the most stable?

A. CH3–
B. C6H5CH2–
C. (CH3)3C–
D. CH2=CH–CH2–

Answer: B. C6H5CH2–
Explanation: Benzyl anion is resonance stabilized by the aromatic ring.
6. In the Diels–Alder reaction, which combination of diene and dienophile leads
to the fastest reaction?

A. Electron-rich diene + electron-rich dienophile

B. Electron-poor diene + electron-poor dienophile
C. Electron-rich diene + electron-poor dienophile
D. Electron-poor diene + electron-rich dienophile

Answer: C. Electron-rich diene + electron-poor dienophile

Explanation: This pairing facilitates interaction between HOMO of diene and LUMO of
dienophile.

7. Which reagent will best convert a ketone to an alkene via Wittig reaction?

A. CH2I2 + Zn(Cu)
B. Ph3P=CH2
C. LDA
D. H2, Pd/C

Answer: B. Ph3P=CH2
Explanation: Wittig reagent (ylide) reacts with ketones or aldehydes to form alkenes.

8. Which statement about SN1 reaction is not correct?

A. It proceeds via carbocation intermediate

B. It shows first-order kinetics
C. Rearrangement is possible
D. It is faster in non-polar solvents
Answer: D. It is faster in non-polar solvents
Explanation: SN1 is favored in polar protic solvents that stabilize the carbocation and leaving
group.

Would you like a PDF of these with explanations or more MCQs on specific topics like
spectroscopy, reaction mechanisms, or name reactions?

4o

You said:

What is meant by rearrangement in question 8

ChatGPT said:

Great question!

In Question 8, the term "rearrangement" refers to a structural shift that occurs after the
formation of a carbocation intermediate in an SN1 reaction.

Here's how it works:

When a leaving group departs in an SN1 reaction, it leaves behind a carbocation, which is an
unstable, positively charged species. To become more stable, this carbocation can rearrange by
shifting a hydride (H–) or an alkyl group from an adjacent carbon. This forms a more stable
carbocation (e.g., secondary → tertiary).

Example of rearrangement:

Let’s say we start with:

2-bromo-3-methylbutane
When it undergoes SN1:

1. Br– leaves, forming a secondary carbocation at C-2.

2. This carbocation rearranges: a hydride shift from the adjacent carbon (C-3) forms a
more stable tertiary carbocation.
3. The nucleophile then attacks this new, more stable carbocation.

Why is this important?

 Rearrangements affect the final product — the nucleophile ends up attaching at a

different carbon than the one where the leaving group originally was.
 Only SN1 allows this because SN2 does not form a carbocation intermediate, so
there's no chance for rearrangement.

Let me know if you'd like a visual diagram of a typical rearrangement!

4o

You said:

Teach by giving example and structures

ChatGPT said:

Perfect! Let’s go step-by-step through a real example of rearrangement in an SN1 reaction,

using structures to make it crystal clear.

Example: 3-Methyl-2-butanol (with HCl)

Let’s say we’re reacting 3-methyl-2-butanol with HCl, which converts the –OH group into a
good leaving group.
Step 1: Formation of the carbocation

We first protonate the alcohol:

markdown
CopyEdit
OH OH2+ H2O leaves
| | |
CH3–CH–CH(CH3)2 → CH3–CH–CH(CH3)2 → CH3–C⁺–CH(CH3)2
| | |
H H H

This gives a secondary carbocation at C-2.

Step 2: Rearrangement

Now, the carbocation is not very stable. But look — the carbon next to it (C-3) is tertiary, and it
can donate a hydride (a hydrogen with its pair of electrons):

mathematica
CopyEdit
Hydride shift from C-3 to C-2:
CH3–C⁺H–CH(CH3)2 → CH3–CH–C⁺(CH3)2
|
H

Now the positive charge is on a tertiary carbon, which is much more stable.

Step 3: Nucleophilic attack

The chloride ion (Cl⁻) now attacks the more stable tertiary carbocation:

mathematica
CopyEdit
CH3–CH–C⁺(CH3)2 + Cl⁻ → CH3–CH–C(Cl)(CH3)2
|
H

Final product: 2-chloro-2-methylbutane

Summary of key points:

 Initial carbocation: formed after the leaving group departs.

 Rearrangement: hydride (or sometimes alkyl) shift occurs to form a more stable
carbocation.
 Result: The product has the nucleophile (Cl⁻) attached at a different position than the
original leaving group.

Would you like me to draw this process out as a clean diagram for easier visualization?

You said:

More MCqs please

ChatGPT said:

Absolutely! Here are more advanced-level organic chemistry MCQs with answers and brief
explanations:

9. Which of the following is a product of the Cannizzaro reaction?

A. Ester
B. Alcohol and carboxylic acid
C. Alcohol and carboxylate salt
D. Ketone and alcohol

Answer: C. Alcohol and carboxylate salt

Explanation: Cannizzaro reaction is a redox reaction of non-enolizable aldehydes in base,
giving one molecule oxidized (to carboxylate) and one reduced (to alcohol).

10. Which of the following compounds undergoes faster SN2 reaction with NaI in
acetone?

A. (CH3)3C–Br
B. CH3CH2CH2Br
C. CH3CHBrCH3
D. CH2=CHCH2Br

Answer: B. CH3CH2CH2Br
Explanation: SN2 reactions are fastest with primary alkyl halides and hindered with tertiary
ones.

11. Which of the following statements is true about the acidity of phenol?

A. Phenol is less acidic than ethanol

B. The phenoxide ion is destabilized by resonance
C. Phenol is more acidic due to resonance stabilization of phenoxide ion
D. The pKa of phenol is greater than that of water

Answer: C. Phenol is more acidic due to resonance stabilization of phenoxide ion

12. The major product in the reaction of 1-butene with B2H6 followed by
H2O2/NaOH is:

A. 1-butanol
B. 2-butanol
C. Butanal
D. Butanoic acid

Answer: A. 1-butanol
Explanation: Hydroboration-oxidation adds OH anti-Markovnikov at the terminal carbon.

13. What is the product when benzene reacts with CH3Cl and AlCl3?

A. Benzyl chloride
B. Toluene
C. Chlorobenzene
D. Benzaldehyde

Answer: B. Toluene
Explanation: Friedel–Crafts alkylation forms toluene (methylbenzene).

14. Which is the correct order of basicity in aqueous solution?

A. Aniline > Methylamine > Ammonia

B. Ammonia > Aniline > Methylamine
C. Methylamine > Ammonia > Aniline
D. Aniline > Ammonia > Methylamine
Answer: C. Methylamine > Ammonia > Aniline
Explanation: Electron-donating groups increase basicity; aromatic systems like aniline
delocalize the lone pair, decreasing availability.

15. Which of the following is most reactive toward electrophilic aromatic

substitution?

A. Nitrobenzene
B. Chlorobenzene
C. Benzene
D. Toluene

Answer: D. Toluene
Explanation: The methyl group is an electron-donating activator, increasing electron density on
the ring.

Want me to continue with more—maybe on named reactions, stereochemistry, or

spectroscopy next?

4o

You said:

Yes named reactions please

ChatGPT said:

Awesome! Here's a set of MCQs focused on named reactions in advanced organic chemistry,
with answers and explanations:
16. The Aldol condensation involves which type of intermediate?

A. Carbocation
B. Carbanion (enolate)
C. Free radical
D. Nitrene

Answer: B. Carbanion (enolate)

Explanation: The reaction proceeds via an enolate ion attacking another carbonyl compound.

17. The product of a Claisen condensation between two esters is:

A. Alcohol
B. Carboxylic acid
C. β-Keto ester
D. Ketone

Answer: C. β-Keto ester

Explanation: Claisen condensation joins two esters, forming a β-keto ester after deprotonation
and elimination.

18. Which of the following reactions is used to form epoxides from alkenes?

A. Wurtz reaction
B. Peracid oxidation (e.g., mCPBA)
C. Wolff–Kishner reduction
D. Sandmeyer reaction

Answer: B. Peracid oxidation (e.g., mCPBA)

Explanation: Alkenes react with peracids to form epoxides in a stereospecific syn addition.
19. In the Wittig reaction, the intermediate formed is a:

A. Carbene
B. Ylide
C. Carbanion
D. Imine

Answer: B. Ylide
Explanation: The Wittig reagent is a phosphonium ylide, which reacts with carbonyl
compounds to give alkenes.

20. Which named reaction is best used to convert an acyl halide into a ketone
using organocopper reagents?

A. Rosenmund reduction
B. Friedel–Crafts acylation
C. Gilman reaction
D. Grignard reaction

Answer: C. Gilman reaction

Explanation: Organocuprates (R2CuLi) react with acyl halides to give ketones selectively.

21. What is the final product of the Beckmann rearrangement of cyclohexanone

oxime?

A. Cyclohexanone
B. Caprolactam
C. Cyclohexylamine
D. Hexanoic acid

Answer: B. Caprolactam
Explanation: Beckmann rearrangement converts ketoximes to amides/lactams. This one forms
caprolactam—a precursor to Nylon-6.

22. The Sandmeyer reaction is used to:

A. Replace diazonium group with Cl, Br, or CN

B. Add bromine to double bonds
C. Remove CO2 from carboxylic acid
D. Add alkyl group to benzene

Answer: A. Replace diazonium group with Cl, Br, or CN

Explanation: Sandmeyer uses Cu(I) salts to substitute aryl diazonium salts with halide or nitrile
groups.