Chapter 18 Multiple Choice Questions

. Which of the following does not undergo conjugate addition with butanamine?

propenal

but-2-enal

ethyl but-3-enoate

butenone

. Which of the following does not undergo an addition reaction with butanamine?

. Which of the following predominantly gives the conjugate addition product with pent-3-en-2-one?

PhMgBr

PhLi

Ph₂CuLi

CH₃MgI

. Which of the following predominantly gives the carbonyl addition product with pent-3-en-2-one?

PhMgBr

PhLi

Ph₂CuLi

CH₃MgI

. Which is the main final product of the following reaction?

. Which is the main product of the following reaction?

. Which is most reactive with sodium methoxide in methanol?

. In which of the following equations is the outcome wrong?

. Which of the following statements is wrong?

o-Chloromethylbenzene gives o- and m-methylanilines upon reaction with sodium amide in liquid ammonia.

o-Chlorotrifluoromethylbenzene gives mainly m-trifluoromethylaniline upon reaction with sodium amide in liquid ammonia.

1-Chloro-2,6-dimethylbenzene does not undergo a substitution reaction with sodium amide in liquid ammonia.

m-Chloromethoxybenzene gives o-, m-, and p-methoxyanilines in an approximate ratio of 1:2:1 upon reaction with sodium amide in liquid ammonia.

. Which of the following does not undergo a conjugate addition reaction with butanamine?

. Which of the following does not selectively give the product of conjugate addition with ethyl but-2-enoate?

NaCN / H₂O

BuLi / THF

BuNH₂

PhSNa / EtOH

. The following sequence shows a synthesis of cyclohex-2-enone. Which combination of reagents is feasible for carrying out steps 1 and 2?

1) Br₂ / NaOH / H₂O, 2) H₂SO₄ / H₂O

1) HBr / AcOH, 2) Et₃N/ EtOH

1) HBr / AcOH, 2) NaOEt / EtOH

1) Br₂ / AcOH, 2) Et₃N/ EtOH

. Which is the main product of the following reaction?

. Which of the following reactions shows a wrong main product?

. Which of the following statements regarding the reaction of cyanide with pent-3-en-2-one in aqueous ethanol is wrong?

An initial product is the cyanohydrin formed by the addition of cyanide to the carbonyl.

Formation of a cyanohydrin is reversible.

At higher temperatures, the main product is by conjugate addition.

Conjugate addition gives 4-cyanopentan-2-ol as the thermodynamic product.

. Which is most reactive with sodium methoxide in methanol?

. Which is the second most reactive with sodium methoxide in methanol?

. Which gives about 1:1 p- and m-methylanilines as the main products when treated with sodium amide in liquid ammonia?

. Which of the following equations shows the wrong outcome of the main reaction?

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