Chemistry - Hydrocarbon Question with Solution | TestHub
Answer the following questions based on given reaction
Total number of theoretically products (including stereo)
Options:
Answer:
Solution:
Question Explanation:
The question asks how many distinct products are theoretically possible when the given substituted
cyclopropane undergoes free-radical monochlorination, counting all constitutional and stereoisomers.
Concept: This question is based on free radical halogenation reaction.
Solution:
Substitution on CH3 (a): Product is 1-chloro-1-ethylcyclopropane. No chiral center. → 1 product
Substitution on CH2 (b): Product is 1-(1-chloroethyl)cyclopropane. One chiral center. → 2
products (R and S enantiomers).
Substitution on C1H (c): Product is 1-chloro-1-ethylcyclopropane. No chiral center. → 1 product.
(Wait, this is the same structural isomer as (1). Let's re-read the question. The substitution must be
on a C–H bond. So a, b, c, d are the non-equivalent H atoms. The product from a and c is the same
structural isomer: 1–chloro–1-ethylcyclopropane. → Count as 1 product.)
Substitution on C2H2 or C3H2 (d/e): Product is 2-chloro-1-ethylcyclopropane. Two chiral centers
(C1 and C2 ). This leads to two pairs of enantiomers: cis (R, R and S, S) and trans (R, S and S, R).
→ 4 products.
Free-radical monochlorination occurs at all available C-H bonds. The product is formed by substituting one H atom with one Cl atom.
Total number of products (including stereo): 1 + 2 + 1 + 4 = 8