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(a) Use the relative bond lengths of the CC and CO bonds to predict which of the

Chapter 8, Problem 8.57

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QUESTION:

a) Use the relative bond lengths of the CC and CO bonds to predict which of the following two equilibria lies farther to the right. (That is, predict which of the two compounds contains more of the conformation with the axial methyl group.) (1) (2) (b) Which one of the following compounds contains the greater amount of gauche conformation for internal rotation about the bond shown? Explain.

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QUESTION:

a) Use the relative bond lengths of the CC and CO bonds to predict which of the following two equilibria lies farther to the right. (That is, predict which of the two compounds contains more of the conformation with the axial methyl group.) (1) (2) (b) Which one of the following compounds contains the greater amount of gauche conformation for internal rotation about the bond shown? Explain.

ANSWER:

Step 1 of 3

(a)

Let’s write the equilibrium of the given compounds;

From the above,

Strength of the $$ C-O$$ bond is more than that of the $$ C- C$$ bond.

Bond length of $$ C-O$$ bond is smaller than that of the $$ C- C$$bond.

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