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Heterolytic Cleavage

Using curved-...

Question

Using curved-arrow notation, show the formation of reactive intermediates when the following covalent bonds undergo heterolytic cleavage.
a. $C H_{3} - C S H_{3}$
b. $C H_{3} - C N$
c. $C H_{3} - C u$

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Solution

(Cu is more electropositive than C).

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Similar questions

Q. Which of the following intermediate is formed, due to heterolytic cleavage of

C - C l

C H_{3} C l

Q. Classify the reagents shown in bonds in the following equations as nucleophiles or electrophiles. Use curved-arrow notation to show the electron movement.
a.

C H_{3} C O O H + H O^{⊖} \to C H_{3} C O O^{⊖} + H_{2} O

C H_{3} C O C H_{3} + N C^{⊖} \to C H_{3} C (C N) O H C H_{3}

C_{6} H_{6} + C H_{3} ⊖ C O \to C_{6} H_{5} C O C H_{3}

Q. Which one of the following alcohols is most reactive for

S_{N} 1

reaction?

$(a) C H_{3} - O H | C | C H_{3} - C H_{3} (b) C_{6} H_{5} - O H | C | C H_{3} - C_{6} H_{5}$
$(c) C H_{3} - O H | C | C H_{3} - C H_{3} (d) C H_{3} - O H | C - C H_{3}$

C H_{3} - O | | C - C H_{3}

X_{2}, O H^{-} - ---- \to

C H_{3} - O | | C - C H_{3}

\to X_{3} C - O | | C - C X_{3}

The trihaloketone also undergoes hydrolysis in present of OH forming

C H_{3} - O | | C - C H_{3}

O H^{-} - -- \to

C H_{3} - O | | C - O^{-} - C H X_{3}

During formation of trihaloketone, which halogen is introduced most easily?

Q. (a) Arrange the following compounds in the increasing order of their acid strength:
p - cresol, p - nitrophenol, phenol
(b) Write the mechanism (using curved arrow notation) of the following reaction:

C H_{2} = C H_{2} H_{3} O^{+} - -- \to C H_{3} - C H_{2}^{+} + H_{2} O

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