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Chapter 9: Q10cP (page 278)

Show the terminal alkyne and alkyl halide from which the following products can be obtained. If two routes look feasible, list both.

Short Answer

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Alkylation

Migration of the alkyl group from one molecule to another via carbanion or carbocation formation

Alkylation of acetylide ion

Acetylide ion is a strong nucleophile which reacts with the electrophile like alkyl halide that replace the halide and form alkyne. Hence new C-C bond is formed and old C-Br bond is broke.

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Most popular questions from this chapter

A hydrocarbon of unknown structure has the formula C₈H₁₀. On catalytic hydrogenation over the Lindlar catalyst, 1 equivalent of H₂ is absorbed. On hydrogenation over a palladium catalyst, 3 equivalents of H₂ are absorbed.

(a) How many degrees of unsaturation are present in the unknown structure?

(b) How many triple bonds are present?

(d) How many rings are present?

(e) Draw a structure that fits the data.

Let be a group and assume that for each positive integer i , N_i is a normal subgroup of G. If every element of can be written uniquely in the form n_i1 .n_i2 ...n_ikwith i₁ < i₂ < ... < i_k and n_ij $\in$ N_ij , prove that G $≅$ $\sum_{i = 1}$ N_i (see Exercise 34). [Hint: Adapt the proof of Theorem 9.1 by defining f(a₁, a₂...) to be the product of those a_i that are not the identity element.]

Show the terminal alkyne and alkyl halide from which the following products can be obtained. If two routes look feasible, list both.

$a . {CH}_{3} {CH}_{2} {CH}_{2} C \equiv CH$

A cumulene is a compound with three adjacent double bonds. Draw an orbital picture of a cumulene. What kind of hybridization do the two central carbon atoms have? What is the geometric relationship of the substituents on one end to the substituents on the other end? What kind of isomerism is possible? Make a model to help see the answer.

$R_{2} C = C = C = {CR}_{2}$

A cumulene

Propose structures for hydrocarbons that give the following products

on oxidative cleavage by KMnO₄ or O₃ :