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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 chemical reaction is one in which old bonds are broken and new bonds are made. During the course of these changes a variety of intermediates are formed before a starting material is converted to final products. Formation of these intermediates depend on several factors like bond energies, kinetics of the reactions etc. Identify the correct statement among the following. (a) An electrophile has always a positive charge. (b) \(\mathrm{CN}^{-}\) can act as an ambident nucleophile. (c) The carbon species A formed is a methyl carbanion. (d) In \(\mathrm{CH}_{3} \mathrm{MgBr}\), the methyl group carries slight positive charge.

Four pairs of compounds (A) - (D) are given below. Indicate, in each pair, which compound can be more effectively hydrogen bonded. (a) \(\mathrm{CH}_{3} \underset{(\mathrm{I})}{\mathrm{CH}_{2}} \mathrm{OH}\) and \(\mathrm{CH}_{3}-\underset{(\mathrm{IH})}{\mathrm{O}-\mathrm{CH}_{3}}\) (b) \(\underset{\text { (I) }}{\left(\mathrm{CH}_{3}\right)}_{3} \mathrm{~N}\) and \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (c) \(\mathrm{HOCH}_{2}-\left(\mathrm{CH}_{2}\right)_{4}-\mathrm{CH}_{2} \mathrm{OH}\) and \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}_{\text {(II) }}{\mathrm{C}} \mathrm{HOHCH}_{3}\) (d) \(\mathrm{CH}_{3} \underset{\text { (I) }}{\mathrm{CH}_{2}} \mathrm{OH}\) and \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{SH}\) (a) \((\mathrm{A})-(\mathrm{I}),(\mathrm{B})-(\mathrm{I}),(\mathrm{C})-(\mathrm{I}),(\mathrm{D})-(\mathrm{I})\) (b) (A) - (I), (B) - (II), (C) - (I), (D) - (II) (c) \((\mathrm{A})-(\mathrm{I}),(\mathrm{B})-(\mathrm{I}),(\mathrm{C})-(\mathrm{II}),(\mathrm{D})-(\mathrm{II})\) (d) (A) - (I), (B) - (II), (C) - (I), (D) - (I)

Identify the statement which is not correct among the following. (a) Acetone exists almost \(100 \%\) in the keto form. (b) Acetylacetone exists considerably in the enol form. (c) Phenol exists almost \(100 \%\) in the enol form. (d) The enol content of \(\mathrm{C}_{6} \mathrm{H}_{c}-\mathrm{COCH}_{2} \mathrm{C}_{6} \mathrm{H}_{5}\) is very low.

The least stable cabocation among the following is (a) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}^{+}\) (b) \(\mathrm{F}_{3} \mathrm{C}-\mathrm{CH}_{2}\) (c) \(\mathrm{F}_{3} \mathrm{C}\) (d) \(\mathrm{CH}_{3}-\mathrm{CH}=\stackrel{+}{\mathrm{C}} \mathrm{H}\)

The IUPAC name of (a) 3 -Methyl pent- 2 -en- 1 -ol (b) 2 -Ethyl pent- 2 -en-5-ol (c) 3 -Ethyl-but-2-en-1-ol (d) 3 , 3 -Methyl ethyl prop-2-en-1-ol
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