The major product of the following reaction is:
The image details a multi-halogenated hydrocarbon chain reacting with excess ethanolic potassium hydroxide under heating conditions.
A.6-Phenylhepta-2,4-diene
B.2-Phenylhepta-2,5-diene
C.6-Phenylhepta-3,5-diene
D.2-Phenylhepta-2,4-diene
Solution & Explanation
### Related Formula
Base-induced dehydrohalogenation follows the Zaitsev rule to maximize thermodynamic stability via conjugated double bond networks:
R-CHX-CH_2-CHX-R' xrightarrowtextexcess KOH/EtOH, Delta textConjugated Diene$$R-CHX-CH_2-CHX-R' \xrightarrow{\text{excess } KOH/EtOH, \Delta} \text{Conjugated Diene}$$
### Core Logic
The reactant is a dihalide containing a phenyl substitution. Treating with excess alcoholic KOH$KOH$ and heat induces double dehydrohalogenation via successive E2$E2$ elimination pathways.
The eliminations occur to yield the most stable, highly conjugated product where the double bonds are conjugated with each other and, if possible, with the aromatic phenyl ring system.
### Step 1: Eliminating and Tracking Conjugation
Eliminating the first and second equivalents of HBr$HBr$ sets up a conjugated diene system along the heptadiene chain.
Tracing carbon numbers correctly from the end closest to the phenyl ring reveals that the conjugated diene centers sit across carbons 2 and 4, producing **2-Phenylhepta-2,4-diene**.
The image details a multi-halogenated hydrocarbon chain reacting with excess ethanolic potassium hydroxide under heating conditions.
### Pattern Recognition
When dealing with excess elimination agents on dihalides, look for options that form a *continuous conjugated diene* structure (alternating double-single-double bonds). This conjugation offers significant thermodynamic stability, especially when directly extended from a phenyl group.
### Evaluation Rubric / Model Answer
null
### Chapter Mix
Class 12 Chemistry: Haloalkanes and Haloarenes
The image details a multi-halogenated hydrocarbon chain reacting with excess ethanolic potassium hydroxide under heating conditions.
More Haloalkanes and Haloarenes Previous-Year Questions
Q54jee_main_2026_21_jan_morningReactions of Haloalkanes
A hydrocarbon ‘P’ (C_4H_8$C_{4}H_{8}$) on reaction with HCl gives an optically active compound ‘Q’ (C_4H_9Cl$C_{4}H_{9}Cl$) which on reaction with one mole of ammonia gives compound ‘R’ (C_4H_11N$C_{4}H_{11}N$). ‘R’ on diazotization followed by hydrolysis gives ‘S’. Identify P, Q, R and S.
### Core Logic
Since P (C_4H_8$C_4H_8$) reacts with HCl to give an optically active compound Q (C_4H_9Cl$C_4H_9Cl$), P must be But-2-ene. Addition of HCl yields 2-chlorobutane, which possesses a chiral center.
mathrmCH_3-mathrmCH=mathrmCH-mathrmCH_3 xrightarrowmathrmHCl mathrmCH_3-mathrmCH_2-mathrmC^*mathrmH(mathrmCl)-mathrmCH_3 quad text(P is But-2-ene, Q is 2-chlorobutane)$$\mathrm{CH}_3-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}_3 \xrightarrow{\mathrm{HCl}} \mathrm{CH}_3-\mathrm{CH}_2-\mathrm{C}^*\mathrm{H}(\mathrm{Cl})-\mathrm{CH}_3 \quad \text{(P is But-2-ene, Q is 2-chlorobutane)}$$Reactions of Haloalkanes diagram for Q54 - JEE Main 2026 Morning
Compound Q reacts with mathrmNH_3$\mathrm{NH}_3$ to undergo nucleophilic substitution forming a primary amine R:
mathrmCH_3-mathrmCH_2-mathrmCH(mathrmCl)-mathrmCH_3 xrightarrowmathrmNH_3 mathrmCH_3-mathrmCH_2-mathrmCH(mathrmNH_2)-mathrmCH_3 quad text(R is Butan-2-amine)$$\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}(\mathrm{Cl})-\mathrm{CH}_3 \xrightarrow{\mathrm{NH}_3} \mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}(\mathrm{NH}_2)-\mathrm{CH}_3 \quad \text{(R is Butan-2-amine)}$$Reactions of Haloalkanes diagram for Q54 - JEE Main 2026 Morning
Diazotization of primary aliphatic amines followed by hydrolysis yields an alcohol via a carbocation intermediate (S):
mathrmCH_3-mathrmCH_2-mathrmCH(mathrmNH_2)-mathrmCH_3 xrightarrowmathrmNaNO_2 / mathrmHCl / mathrmH_2mathrmO mathrmCH_3-mathrmCH_2-mathrmCH(mathrmOH)-mathrmCH_3 quad text(S is Butan-2-ol)$$\mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}(\mathrm{NH}_2)-\mathrm{CH}_3 \xrightarrow{\mathrm{NaNO}_2 / \mathrm{HCl} / \mathrm{H}_2\mathrm{O}} \mathrm{CH}_3-\mathrm{CH}_2-\mathrm{CH}(\mathrm{OH})-\mathrm{CH}_3 \quad \text{(S is Butan-2-ol)}$$Reactions of Haloalkanes diagram for Q54 - JEE Main 2026 Morning
### Pattern Recognition
An optically active alkyl halide formed from a C_4H_8$C_4H_8$ alkene with HX is a classic pointer to 2-halobutane originating from But-2-ene or But-1-ene. Diazotization of primary aliphatic amines (R-NH_2$R-NH_2$) with NaNO_2/HCl$NaNO_2/HCl$ yields alcohols (R-OH$R-OH$) with possible rearrangements, though here a secondary carbocation is already stable.
### Evaluation Rubric / Model Answer
null
### Chapter Mix
Class 12 Chemistry: Haloalkanes and Haloarenes
Class 12 Chemistry: Amines
Qjee_main_2025_02_april_eveningChemical Reactions and Named Rules
### Related Formula
textNamed Organic Transformations$$\text{Named Organic Transformations}$$
### Core Logic
Let us systematically match each reaction in List-I to its standardized organic reaction name in List-II:
- **Reaction (A)**: Coupling of two aryl halides with sodium metal in dry ether to form biaryl is the classic **Fittig reaction** rightarrow$\rightarrow$ **(III)**.
- **Reaction (B)**: Conversion of benzene diazonium chloride to aryl halide using copper powder (mathrmCu$\mathrm{Cu}$) in halogen acids like mathrmHCl$\mathrm{HCl}$ is the **Gatterman reaction** rightarrow$\rightarrow$ **(IV)**.
- **Reaction (C)**: Substitution of halogen in an alkyl halide with sodium iodide (mathrmNaI$\mathrm{NaI}$) in dry acetone solvent is the classic halogen exchange method called the **Finkelstein reaction** rightarrow$\rightarrow$ **(II)**.
- **Reaction (D)**: Replacement of the hydroxyl group in tertiary butyl alcohol with chlorine using conc. mathrmHCl$\mathrm{HCl}$ in the presence of anhydrous mathrmZnCl_2$\mathrm{ZnCl_2}$ catalyst is the **Lucas reaction** rightarrow$\rightarrow$ **(I)**.
### Step 1: Selection
Combining the selections, the correct sequence is:
**(A)-(III), (B)-(IV), (C)-(II), (D)-(I)**
This maps directly to option (2).
### Pattern Recognition
Named reaction matching questions are very straightforward. Keep a clear distinction between the Sandmeyer reaction (which uses cuprous halide, e.g. mathrmCu_2Cl_2$\mathrm{Cu_2Cl_2}$) and the Gatterman reaction (which uses copper powder, mathrmCu$\mathrm{Cu}$).
### Evaluation Rubric / Model Answer
null
### Chapter Mix
Class 12 Chemistry: Haloalkanes and Haloarenes
Q48jee_main_2025_02_april_eveningElimination and Addition Reaction Sequences
Consider the following sequence of reactions:
mathrmCH_3-CH_2-CH_2-CH(Br)-CH_3 xrightarrowtextalcoholic KOH mathrmP text (Major Product) xrightarrowmathrmBr_2 mathrmQ$$\mathrm{CH_3-CH_2-CH_2-CH(Br)-CH_3} \xrightarrow{\text{alcoholic KOH}} \mathrm{P} \text{ (Major Product)} \xrightarrow{\mathrm{Br_2}} \mathrm{Q}$$
Consider the above sequence of reactions. 151~mathrmg$151~\mathrm{g}$ of 2-bromopentane is made to react. Yield of major product mathrmP$\mathrm{P}$ is 80\%$80\%$ whereas mathrmQ$\mathrm{Q}$ is 100\%$100\%$.
Mass of product mathrmQ$\mathrm{Q}$ obtained is _______ g.
Given molar mass in mathrmg~mol^-1$\mathrm{g~mol^{-1}}$ H: 1, C: 12, O: 16, Br: 80
Numerical Answer.Answer: 184 to 184
Solution
### Related Formula
textActual Yield = textTheoretical Yield times \% text Yield$$\text{Actual Yield} = \text{Theoretical Yield} \times \% \text{ Yield}$$
### Core Logic
Let us break down each chemical reaction step:
- **Step 1**: 2-bromopentane undergoes dehydrohalogenation via an E2 mechanism using alcoholic mathrmKOH$\mathrm{KOH}$. According to Saytzeff's rule, the more substituted alkene is the major product. Thus, **pent-2-ene** is the major product mathrmP$\mathrm{P}$.
Chemical reaction showing elimination of 2-bromopentane to form pent-2-ene
- **Step 2**: Pent-2-ene undergoes electrophilic bromination with liquid bromine (mathrmBr_2$\mathrm{Br_2}$) to give **2,3-dibromopentane** (product mathrmQ$\mathrm{Q}$):
Chemical reaction showing elimination of 2-bromopentane to form pent-2-ene
### Step 1: Calculate Initial Moles of Reactant
Calculate the molar mass of 2-bromopentane (mathrmC_5H_11Br$\mathrm{C_5H_{11}Br}$):
textMolar mass = 5(12) + 11(1) + 80 = 60 + 11 + 80 = 151~mathrmg~mol^-1$$\text{Molar mass} = 5(12) + 11(1) + 80 = 60 + 11 + 80 = 151~\mathrm{g~mol^{-1}}$$textInitial moles = frac151~mathrmg151~mathrmg~mol^-1 = 1~mathrmmol$$\text{Initial moles} = \frac{151~\mathrm{g}}{151~\mathrm{g~mol^{-1}}} = 1~\mathrm{mol}$$
### Step 2: Calculate Moles of Intermediate P and Q
Since the yield of mathrmP$\mathrm{P}$ is 80\%$80\%$:
textMoles of P formed = 1 times 0.80 = 0.8~mathrmmol$$\text{Moles of P formed} = 1 \times 0.80 = 0.8~\mathrm{mol}$$
Since the conversion of mathrmP rightarrow mathrmQ$\mathrm{P} \rightarrow \mathrm{Q}$ has a yield of 100\%$100\%$, the mole count remains stoichiometric:
textMoles of Q formed = 0.8 times 1.00 = 0.8~mathrmmol$$\text{Moles of Q formed} = 0.8 \times 1.00 = 0.8~\mathrm{mol}$$
### Step 3: Calculate Mass of Q
Product mathrmQ$\mathrm{Q}$ is 2,3-dibromopentane (mathrmC_5H_10Br_2$\mathrm{C_5H_{10}Br_2}$).
Calculate its molar mass:
textMolar mass of Q = 5(12) + 10(1) + 2(80) = 60 + 10 + 160 = 230~mathrmg~mol^-1$$\text{Molar mass of Q} = 5(12) + 10(1) + 2(80) = 60 + 10 + 160 = 230~\mathrm{g~mol^{-1}}$$textMass of Q = 0.8 times 230 = 184~mathrmg$$\text{Mass of Q} = 0.8 \times 230 = 184~\mathrm{g}$$
### Pattern Recognition
Saytzeff vs Hofmann: Alcoholic mathrmKOH$\mathrm{KOH}$ is a small, non-bulky base, which selectively targets the internal secondary proton to yield the thermodynamic trans-alkene (pent-2-ene) as the major product rather than the terminal 1-alkene.
### Evaluation Rubric / Model Answer
null
### Chapter Mix
Class 12 Chemistry: Haloalkanes and Haloarenes
Qjee_main_2025_02_april_morningReactions of Alkyl Halides and Alkyne Hydration
An optically active alkyl halide mathrmC_4H_9Br$\mathrm{C_4H_9Br}$ [A] reacts with hot KOH dissolved in ethanol and forms alkene [B] as major product which reacts with bromine to give dibromide [C]. The compound [C] is converted into a gas [D] upon reacting with alcoholic mathrmNaNH_2$\mathrm{NaNH_2}$. During hydration 18 gram of water is added to 1 mole of gas [D] on warming with mercuric sulphate and dilute acid at 333mathrmK$333\mathrm{K}$ to form compound [E]. The IUPAC name of compound [E] is :
A.(1)\ textBut-2-yne$(1)\ \text{But-2-yne}$
B.(2)\ textButan-2-ol$(2)\ \text{Butan-2-ol}$
C.(3)\ textButan-2-one$(3)\ \text{Butan-2-one}$
D.(4)\ textButan-1-al$(4)\ \text{Butan-1-al}$
Solution
### Related Formula
Dehydrohalogenation via alcoholic KOH follows E2 elimination mechanism:
mathrmR-CH_2-CH(Br)-R' xrightarrowtextalc. KOH R-CH=CH-R'$$\mathrm{R-CH_2-CH(Br)-R' \xrightarrow{\text{alc. KOH}} R-CH=CH-R'}$$
Hydration of alkynes using mathrmHgSO_4/H_2SO_4$\mathrm{HgSO_4/H_2SO_4}$ yields ketones via keto-enol tautomerism.
### Core Logic
Let's trace the full sequence line-by-row:
1. **[A]** is an optically active halide with formula mathrmC_4H_9Br rightarrow mathrmCH_3-CH(Br)-CH_2-CH_3$\mathrm{C_4H_9Br} \rightarrow \mathrm{CH_3-CH(Br)-CH_2-CH_3}$ (2-Bromobutane).
2. Reaction of [A] with hot ethanolic KOH produces **[B]** as the major product: mathrmCH_3-CH=CH-CH_3$\mathrm{CH_3-CH=CH-CH_3}$ (But-2-ene).
3. Treatment of [B] with mathrmBr_2$\mathrm{Br_2}$ yields a vicinal dibromide **[C]**: mathrmCH_3-CH(Br)-CH(Br)-CH_3$\mathrm{CH_3-CH(Br)-CH(Br)-CH_3}$ (2,3-Dibromobutane).
4. Reaction of [C] with alcoholic mathrmNaNH_2$\mathrm{NaNH_2}$ converts it via double dehydrohalogenation into gas **[D]**: mathrmCH_3-Cequiv C-CH_3$\mathrm{CH_3-C\equiv C-CH_3}$ (But-2-yne).
5. Hydration of 1 mole of [D] with mathrmH_2O$\mathrm{H_2O}$ in the presence of mathrmHg^2+/H^+$\mathrm{Hg^{2+}/H^+}$ forms an enol intermediate that rapidly tautomerizes to compound **[E]**: mathrmCH_3-CO-CH_2-CH_3$\mathrm{CH_3-CO-CH_2-CH_3}$ (Butan-2-one).
### Step 1: Visualization
Reaction roadmap step verification for Q27
### Pattern Recognition
Whenever you see a 4-carbon chain undergoing terminal/internal dehydrohalogenation followed by hydration of the resulting alkyne, look closely at the configuration: symmetric or unsymmetric alkyne hydration both systematically lead to Butan-2-one because a stable ketone cannot form on position 1 via standard Kucherov hydration of an internal chain.
### Evaluation Rubric / Model Answer
null
### Chapter Mix
Class 12 Physics: Haloalkanes and Haloarenes
Class 11 Chemistry: Hydrocarbons
Class 12 Chemistry: Aldehydes, Ketones and Carboxylic Acids
Qjee_main_2025_08_april_eveningPreparation and Reactions of Styrene derivatives
Choose the correct set of reagents for the following conversion:
textEthyl benzene longrightarrow text4-bromostyrene$$\text{Ethyl benzene} \longrightarrow \text{4-bromostyrene}$$
{{Q_IMG1}}
The figure illustrates the multi-step conversion starting from ethylbenzene to yield a brominated styrene derivative.The figure illustrates the multi-step conversion starting from ethylbenzene to yield a brominated styrene derivative.
### Core Logic
To synthesize 4-bromostyrene starting from ethyl benzene, we must carry out ring functionalization prior to developing the side-chain double bond:
1. **Ring Bromination**: Treatment of ethylbenzene with textBr_2$\text{Br}_2$ in the presence of textFe$\text{Fe}$ (or textFeBr_3$\text{FeBr}_3$) acts via electrophilic aromatic substitution. The ethyl group is an ortho/para director, yielding 1-bromo-4-ethylbenzene as the major product owing to steric mitigation.
2. **Side-Chain Halogenation**: Free radical substitution with textCl_2$\text{Cl}_2$ under thermal conditions (Delta$\Delta$) or UV light specifically chlorinates the benzylic position because the benzylic radical is exceptionally stable via resonance.
3. **Elimination**: Heating with alcoholic textKOH$\text{KOH}$ drives an E2$E2$ elimination of the benzylic chloride, cleanly synthesizing the terminal alkene linkage of the styrene system. The figure illustrates the multi-step conversion starting from ethylbenzene to yield a brominated styrene derivative.
### Pattern Recognition
If you perform side-chain halogenation/alkene generation first, the ring substitution later would lack para-selectivity control and risk reacting across the alkene path. Hence, ring substitution MUST precede double bond creation.
### Evaluation Rubric / Model Answer
null
### Chapter Mix
Class 12 Chemistry: Haloalkanes and Haloarenes
Class 11 Chemistry: Hydrocarbons
More Haloalkanes and Haloarenes Questions — jee_main_2025_28_jan_evening
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