What is the stability order of singlet Halocarbene?

${CF}_{2} > {CI}_{2} > {CCI}_{2} > {CBr}_{2}$

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${CF}_{2} > {CCI}_{2} > {CBr}_{2} > {CI}_{2}$

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${CI}_{2} > {CBr}_{2} > {CCI}_{2} > {CF}_{2}$

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${CCI}_{2} > {CF}_{2} > {CBr}_{2} > {CI}_{2}$

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Solution

The correct option is B
${CF}_{2} > {CCI}_{2} > {CBr}_{2} > {CI}_{2}$

Explanation for correct option;
B. ${CF}_{2} > {CCI}_{2} > {CBr}_{2} > {CI}_{2}$
Singlet carbene:
Singlet carbene are have two lone pairs within the same orbital, so repulsion between electrons is more.
Singlet carbene has a vacant p orbital so back bonding is feasible.
The single carbene will stabilize with substituents that can donate electron pairs such as halogens by delocalizing the pair into an empty p-orbital.
The singlet carbene is more stable than the triplet carbene when there is a substituent with lone pairs in the singlet carbene.
The stability of carbenes decreases in the inductive withdrawal.
The electron-withdrawing trend in halogens will be $F > Cl > Br > I$ .
Thus, the stability order of singlet halocarbene is ${CF}_{2} > {CCI}_{2} > {CBr}_{2} > {CI}_{2}$ .
Explanation for incorrect options:
The trend for the stability of singlet halocarbene is ${CF}_{2} > {CCI}_{2} > {CBr}_{2} > {CI}_{2}$ . Thus, options A, C, and D are incorrect.
Hence, the correct option is B i.e. ${CF}_{2} > {CCI}_{2} > {CBr}_{2} > {CI}_{2}$ .

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