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Chapter 1: Problem 106

Four pairs of compounds are given below. In each pair, one is chiral while the other is achiral. Identify in each pair which is chiral. Choose from the options given I \(\quad \mathrm{ClCH}_{2} \mathrm{CHOHCH}_{2} \mathrm{OH}\) and \(\mathrm{HOH}_{2} \mathrm{C.CHClCH}_{2} \mathrm{OH}\) (A) (B) II \(\quad \mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{Br}\) and \(\mathrm{CH}_{3} \mathrm{CHBrCH}=\mathrm{CH}_{2}\) (A) (B) The options are (b) I A IV B \(\begin{array}{lllll}\text { (c) I A } & \text { II A } & \text { III B } & \text { IV A }\end{array}\) \(\begin{array}{lllll}\text { (d) I B II B III B } & \text { IV A }\end{array}\)

Short Answer

Expert verified
Pair I: A) ClCH2CHOHCH2OH B) HOH2C.CHClCH2OH Pair II: A) CH3CH=CHCH2Br B) CH3CHBrCH=CH2 Answer: The chiral compounds in each pair are: - Pair I: Option A (ClCH2CHOHCH2OH) - Pair II: Option B (CH3CHBrCH=CH2)

Step by step solution

01

Pair I Analysis

Examine the two compounds in Pair I and determine if there is a chiral center in either of them. 1. ClCH2CHOHCH2OH has a carbon atom with the following four different groups attached: Cl, HOH, H, and CH2OH. Therefore, it is chiral. 2. HOH2C.CHClCH2OH does not have a carbon atom with four different groups attached. Therefore, it is achiral.
02

Pair II Analysis

Examine the two compounds in Pair II and determine if there is a chiral center in either of them. 1. CH3CH=CHCH2Br does not have a carbon atom with four different groups attached. However, note that the presence of the double bond (CH=CH) results in restricted rotation, leading to potential geometric isomers (cis or trans). This compound does not have a chiral center, but can still be considered chiral due to the presence of geometric isomers. 2. CH3CHBrCH=CH2 has a chiral carbon atom (the second carbon from the left) with the following four different groups attached: CH3, Br, H, and CH=CH2. Therefore, it is chiral.
03

Conclusion

The chiral compounds among the given pairs are - Pair I: ClCH2CHOHCH2OH (Option A) - Pair II: CH3CHBrCH=CH2 (Option B) Thus, the correct combination is (c) I A II B.

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Most popular questions from this chapter

A compound with molecular formula \(\mathrm{C}_{7} \mathrm{H}_{16}\) exhibits optical isomerism. The compound is (a) 2,5 dimethylhexane (b) \(2-2\) -dimethylpentane (c) 3 -methylpentane (d) 2,3 -dimethylpentane

In which of the following reactions, new chiral centre(s) is/are generated. (a) \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}_{3} \stackrel{\text { Baeyer'sreagent }}{\longrightarrow}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}-\mathrm{CH}_{3}+\mathrm{HBr} \rightarrow\) (c) (d) \(\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}_{2}+\mathrm{HCl} \rightarrow\)

Zero inductive effect is shown by (a) \(-\mathrm{CH}_{3}\) (b) \(-\mathrm{H}\) (c) \(-\mathrm{D}\) (d) \(-\mathrm{C}_{6} \mathrm{H}_{5}\)

The IUPAC name of \(\quad 1\) is CCC(C)CC(CC)CC (a) 5 -heptenylheptane (b) 3 -heptylhept-3-ene (c) 3 -(3-heptyl) hept-3-ene (d) 5,6-Diethyl-3-methyldec-4-ene

Which of the following are correct statements? (a) \(\mathrm{BF}_{3}\) and are: \(\mathrm{CCl}_{2}\) electrophiles. (b) Dimethylsulphoxide and dimethyl formamide (DMF) are aprotic solvents. (c) In butadiene \(\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}-\mathrm{CH}=\mathrm{CH}_{2}\) all the three \(\mathrm{C}-\mathrm{C}\) bond lengths are equal. (d) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{Cl}\) has low reactivity because chlorine is attached to an \(\mathrm{sp}^{2}\) carbon.
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