Sign in
12thPass logo
New chatPYQ LibraryDoubtsRank report
Sign in to see Recents

Your guest activity stays on this device

Sign in to save progress →
Sign in

Basics of Organic Chemistry question

2020 · Shift 1 · Q4
Guest · filters and generic practice availableBrowsing as a guest · PYQ filters and generic practice are available. Sign in only for personalised features and saved progress.
  1. PYQ Library
  2. /JEE Advanced
  3. /Chemistry
  4. /Basics of Organic Chemistry
  5. /2020 · Shift 1 · Q4

Basics of Organic Chemistry question

2020 · Shift 1 · Q4

JEE AdvancedChemistryBasics of Organic ChemistryMCQ+3 / −1
Newman projections P, Q, R and S are shown below : JEE Advanced 2020 Paper 1 Offline Chemistry - Basics of Organic Chemistry Question 31 English Which one of the following options represents identical molecules?
  1. A
    P and Q
  2. B
    Q and S
  3. C
    Q and R
  4. D
    R and S
View written solutionFree

Correct answer: P AND R

Step-by-step analysis:

The problem requires us to identify which pair of Newman projections represents identical molecules. To do this, we will determine the chemical structure and IUPAC name for each molecule represented by the projections P, Q, R, and S.

1. Analysis of Newman Projection P:

  • Front carbon (dot) is attached to: H, H, CH3CH_3CH3​.
  • Back carbon (circle) is attached to: H, CH3CH_3CH3​, C2H5C_2H_5C2​H5​.
  • To determine the structure, we identify the longest carbon chain that passes through the central C-C bond. The longest chain is from the CH3CH_3CH3​ on the front carbon, through the central bond, to the C2H5C_2H_5C2​H5​ group on the back carbon.
  • The chain is CH3−C(front)−C(back)−C2H5CH_3 - C(front) - C(back) - C_2H_5CH3​−C(front)−C(back)−C2​H5​. Let's expand C2H5C_2H_5C2​H5​ to CH2CH3CH_2CH_3CH2​CH3​. The chain is CH3−C(front)−C(back)−CH2−CH3CH_3 - C(front) - C(back) - CH_2 - CH_3CH3​−C(front)−C(back)−CH2​−CH3​.
  • This is a 5-carbon chain (pentane). Let's number it: C(1)H3−C(2)−C(3)−C(4)H2−C(5)H3C(1)H_3 - C(2) - C(3) - C(4)H_2 - C(5)H_3C(1)H3​−C(2)−C(3)−C(4)H2​−C(5)H3​.
  • The front carbon is C2, which is attached to two H atoms (in the main chain view).
  • The back carbon is C3, which is attached to one H and one CH3CH_3CH3​ group.
  • The structure is CH3−CH2−CH(CH3)−CH2−CH3CH_3 - CH_2 - CH(CH_3) - CH_2 - CH_3CH3​−CH2​−CH(CH3​)−CH2​−CH3​.
  • The IUPAC name is 3-methylpentane.

2. Analysis of Newman Projection Q:

  • Front carbon is attached to: H, H, C2H5C_2H_5C2​H5​.
  • Back carbon is attached to: H, H, C2H5C_2H_5C2​H5​.
  • The longest chain runs from the C2H5C_2H_5C2​H5​ on the front carbon to the C2H5C_2H_5C2​H5​ on the back carbon.
  • The structure is C2H5−C(front)H2−C(back)H2−C2H5C_2H_5 - C(front)H_2 - C(back)H_2 - C_2H_5C2​H5​−C(front)H2​−C(back)H2​−C2​H5​.
  • Expanding the ethyl groups: (CH3CH2)−CH2−CH2−(CH2CH3)(CH_3CH_2) - CH_2 - CH_2 - (CH_2CH_3)(CH3​CH2​)−CH2​−CH2​−(CH2​CH3​).
  • This is a straight chain of 6 carbons: CH3−CH2−CH2−CH2−CH2−CH3CH_3-CH_2-CH_2-CH_2-CH_2-CH_3CH3​−CH2​−CH2​−CH2​−CH2​−CH3​.
  • The IUPAC name is Hexane.

3. Analysis of Newman Projection R:

  • Front carbon is attached to: H, CH3CH_3CH3​, C2H5C_2H_5C2​H5​.
  • Back carbon is attached to: H, H, CH3CH_3CH3​.
  • The longest carbon chain runs from the C2H5C_2H_5C2​H5​ on the front carbon to the CH3CH_3CH3​ on the back carbon.
  • The chain is C2H5−C(front)−C(back)−CH3C_2H_5 - C(front) - C(back) - CH_3C2​H5​−C(front)−C(back)−CH3​. Expanding this gives a 5-carbon chain: (CH3CH2)−C(front)−C(back)−CH3(CH_3CH_2) - C(front) - C(back) - CH_3(CH3​CH2​)−C(front)−C(back)−CH3​.
  • Let's number it: C(1)H3−C(2)H2−C(3)−C(4)−C(5)H3C(1)H_3 - C(2)H_2 - C(3) - C(4) - C(5)H_3C(1)H3​−C(2)H2​−C(3)−C(4)−C(5)H3​.
  • The front carbon is C3, which is attached to one H and one CH3CH_3CH3​ group.
  • The back carbon is C4, which is attached to two H atoms.
  • The structure is CH3−CH2−CH(CH3)−CH2−CH3CH_3 - CH_2 - CH(CH_3) - CH_2 - CH_3CH3​−CH2​−CH(CH3​)−CH2​−CH3​.
  • The IUPAC name is 3-methylpentane.

4. Analysis of Newman Projection S:

  • Front carbon is attached to: H, H, CH3CH_3CH3​.
  • Back carbon is attached to: H, CH3CH_3CH3​, CH3CH_3CH3​.
  • The structure is CH3−C(front)H2−C(back)H(CH3)2CH_3 - C(front)H_2 - C(back)H(CH_3)_2CH3​−C(front)H2​−C(back)H(CH3​)2​.
  • Expanding this gives CH3−CH2−CH(CH3)−CH3CH_3 - CH_2 - CH(CH_3) - CH_3CH3​−CH2​−CH(CH3​)−CH3​.
  • The longest carbon chain has 4 carbons (butane). There is a methyl group at position 2.
  • The IUPAC name is 2-methylbutane.

Summary and Conclusion:

  • P: 3-methylpentane
  • Q: Hexane
  • R: 3-methylpentane
  • S: 2-methylbutane

Two molecules are identical if they have the same IUPAC name. From our analysis, molecules P and R are both 3-methylpentane, so they are identical molecules. They represent different conformations (views along different C-C bonds) of the same compound.

Evaluation of Options:

  • A: P (3-methylpentane) and Q (Hexane) are not identical. They are constitutional isomers.
  • B: Q (Hexane, C6H14C_6H_14C6​H1​4) and S (2-methylbutane, C5H12C_5H_12C5​H1​2) are not identical. They have different molecular formulas.
  • C: Q (Hexane) and R (3-methylpentane) are not identical. They are constitutional isomers.
  • D: R (3-methylpentane, C6H14C_6H_14C6​H1​4) and S (2-methylbutane, C5H12C_5H_12C5​H1​2) are not identical. They have different molecular formulas.

Based on a rigorous analysis, the only pair of identical molecules is P and R. This pair is not listed as an option. Therefore, all the given options are incorrect. The stored answer 'C' is also incorrect as Hexane (Q) and 3-methylpentane (R) are different compounds.

There seems to be an error in the question's options or the provided correct answer. The correct pair of identical molecules is P and R.

PreviousNext

More from Basics of Organic Chemistry

  • Which of the following structures has the IUPAC name 3-ethynyl-2-hydroxy-4-methylhex-3-en-5-ynoic acid?2020 · MCQ
  • The Fischer projection of D-erythrose is shown below : D-erythrose and its isomers are listed as P, Q, R, and S in Column - I. Choose the correct relationship of P, Q, R, and S with D-erythrose from Column - II. Includes diagram2020 · MCQ
  • With respect to the compounds I-V, choose the correct statement(s). Includes diagram2020 · Multiple correct
  • Consider the following four compounds, I, II, III, and IV. Choose the correct statement(s) Includes diagram2020 · Multiple correct
  • Total number of isomers, considering both structural and stereoisomers of cyclic ethers with the molecular formula C4​H8​O is .................2019 · Numerical
  • For the given compound X, the total number of optically active stereoisomers is ​. Includes diagram2018 · Numerical
  • Among the following, the number of aromatic compound(s) is Includes diagram2017 · Numerical
  • The correct statements(s) for the following addition reactions is (are) Includes diagram2017 · Multiple correct