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 Consider the above sequence of reactions. 151~mathrmg of 2-bromopentane is made to react. Yield of major product mathrmP is 80\% whereas mathrmQ is 100\%. Mass of product mathrmQ obtained is _______ g. Given molar mass in mathrmg~mol^-1 H: 1, C: 12, O: 16, Br: 80

Numerical Answer Type:
Enter a numerical value Answer: 184 to 184 +4 marks

Solution & Explanation

### Related Formula textActual Yield = textTheoretical 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. According to Saytzeff's rule, the more substituted alkene is the major product. Thus, **pent-2-ene** is the major product mathrmP.
Chemical reaction showing elimination of 2-bromopentane to form pent-2-ene
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) to give **2,3-dibromopentane** (product mathrmQ):
Chemical reaction showing elimination of 2-bromopentane to form pent-2-ene
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): textMolar mass = 5(12) + 11(1) + 80 = 60 + 11 + 80 = 151~mathrmg~mol^-1 textInitial moles = frac151~mathrmg151~mathrmg~mol^-1 = 1~mathrmmol ### Step 2: Calculate Moles of Intermediate P and Q Since the yield of mathrmP is 80\%: textMoles of P formed = 1 times 0.80 = 0.8~mathrmmol Since the conversion of mathrmP rightarrow mathrmQ has a yield of 100\%, the mole count remains stoichiometric: textMoles of Q formed = 0.8 times 1.00 = 0.8~mathrmmol ### Step 3: Calculate Mass of Q Product mathrmQ is 2,3-dibromopentane (mathrmC_5H_10Br_2). Calculate its molar mass: textMolar mass of Q = 5(12) + 10(1) + 2(80) = 60 + 10 + 160 = 230~mathrmg~mol^-1 textMass of Q = 0.8 times 230 = 184~mathrmg ### Pattern Recognition Saytzeff vs Hofmann: Alcoholic mathrmKOH 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

Reference Study Guides

More Haloalkanes and Haloarenes Previous-Year Questions — Page 6

Q67 jee_main_2024_31_jan_evening IUPAC Nomenclature of Haloalkanes
Identify structure of 2,3-dibromo-1-phenylpentane.
  • A. text(1) Structure A
  • B. text(2) Structure B
  • C. text(3) Structure C
  • D. text(4) Structure D

Solution

### Core Logic Decode the IUPAC name: 2,3-dibromo-1-phenylpentane. 1) Parent chain is pentane (5 carbon chain: C1-C2-C3-C4-C5). 2) Substituents: - Phenyl group at position 1. - Bromo groups at positions 2 and 3. Option (3) correctly displays a 5-carbon straight chain. The first carbon attaches to the benzene ring (phenyl group), and the second and third carbons each hold a bromine atom.
IUPAC Nomenclature of Haloalkanes diagram for Q67 - JEE Main 2024 Evening
IUPAC Nomenclature of Haloalkanes diagram for Q67 - JEE Main 2024 Evening
### Evaluation Rubric / Model Answer null ### Chapter Mix Class 12 Chemistry: Haloalkanes and Haloarenes
Q68 jee_main_2024_31_jan_morning Elimination and Addition Reactions
The product (C) in the below mentioned reaction is: CH_3-CH_2-CH_2-Br xrightarrow[Delta]KOH_(alc) A xrightarrow[Delta]HBr B xrightarrow[Delta]KOH_(aq) C
  • A. textPropan-1-ol
  • B. textPropene
  • C. textPropyne
  • D. textPropan-2-ol

Solution

### Step 1: Elimination to form Propene CH_3-CH_2-CH_2-Br xrightarrowtextKOH (alc), Delta CH_3-CH=CH_2 quad text(Compound A: Propene) ### Step 2: Electrophilic Addition of HBr Addition of HBr follows Markovnikov's rule: CH_3-CH=CH_2 + HBr xrightarrowDelta CH_3-CH(Br)-CH_3 quad text(Compound B: 2-Bromopropane) ### Step 3: Nucleophilic Substitution Reaction with aqueous KOH leads to S_N2/S_N1 substitution of Br^- with OH^-: CH_3-CH(Br)-CH_3 xrightarrowtextKOH (aq), Delta CH_3-CH(OH)-CH_3 quad text(Compound C: Propan-2-ol) ### Pattern Recognition Alc. KOH gives elimination (alkene). Aq. KOH gives substitution (alcohol). HBr on unsymmetrical alkene gives Markovnikov addition. ### Evaluation Rubric / Model Answer null ### Chapter Mix Class 12 Chemistry: Haloalkanes and Haloarenes
Q86 jee_main_2024_31_jan_morning Elimination and Substitution
CH_3CH_2Br + NaOH rightarrow textProduct A CH_3CH_2Br + NaOH / H_2O rightarrow textProduct B The total number of hydrogen atoms in product A and product B is
Numerical Answer. Answer: 10 to 10

Solution

### Core Logic Reaction 1: If the reagent is alcoholic NaOH (implied due to formation of a distinct product A to contrast B), elimination occurs: CH_3CH_2Br + NaOH (textalc) rightarrow CH_2=CH_2 text (Ethene) Hydrogen atoms in ethene (C_2H_4) = 4. Reaction 2: If the reagent is aqueous NaOH (NaOH / H_2O), nucleophilic substitution (S_N2) occurs: CH_3CH_2Br + NaOH (textaq) rightarrow CH_3CH_2OH text (Ethanol) Hydrogen atoms in ethanol (C_2H_6O) = 6. Total hydrogen atoms = 4 + 6 = 10. ### Evaluation Rubric / Model Answer null ### Chapter Mix Class 12 Chemistry: Haloalkanes and Haloarenes

More Haloalkanes and Haloarenes Questions — jee_main_2025_02_april_evening

Practice all Haloalkanes and Haloarenes previous-year questions →

Rankbit System
JEE Physics: Waves (+15.5%) | Electrostatics: Concentric Shells (-29.7%) | Modern Physics: Photoelectric Clones (+34.2%) | Mathematics: Definite Integrals (+18.1%) | Chemistry: Coordination Splitting (-11.4%) | JEE Physics: Waves (+15.5%) | Electrostatics: Concentric Shells (-29.7%) | Modern Physics: Photoelectric Clones (+34.2%) | Mathematics: Definite Integrals (+18.1%) | Chemistry: Coordination Splitting (-11.4%)