Benzyl bromide is treated with sodium acetylide then 2 equivalents of HBr. What is the major final product?Select answer from the options below3,3-dibromo-1-phenylbutane1,1-dibromo-4-phenylbutane1,1-dibromo-1-phenylethane2,2-dibromo-1-phenylpropane1,1-dibromo-3-phenylpropaneSave for LaterSubmit Answer
Question
Benzyl bromide is treated with sodium acetylide then 2 equivalents of HBr. What is the major final product?Select answer from the options below3,3-dibromo-1-phenylbutane1,1-dibromo-4-phenylbutane1,1-dibromo-1-phenylethane2,2-dibromo-1-phenylpropane1,1-dibromo-3-phenylpropaneSave for LaterSubmit Answer
Solution
Para resolver esta pregunta, sigamos los pasos de la reacción:
-
Reacción de Benzyl Bromide con Sodium Acetylide:
- Benzyl bromide (C6H5CH2Br) reacciona con sodium acetylide (NaC≡CH).
- El acetiluro de sodio (NaC≡CH) es un nucleófilo fuerte y atacará al carbono del bromo en el benzyl bromide, desplazando al bromo.
- Esto forma un compuesto intermedio: C6H5CH2C≡CH (fenilpropino).
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Tratamiento con 2 equivalentes de HBr:
- La adición de HBr al alquino ocurre en dos etapas.
- En la primera etapa, un equivalente de HBr se adiciona al triple enlace, formando un alqueno: C6H5CH2CH=CHBr.
- En la segunda etapa, el segundo equivalente de HBr se adiciona al doble enlace, formando un alcano: C6H5CH2CHBrCH2Br.
El producto final es 1,1-dibromo-3-fenilpropano.
Por lo tanto, la respuesta correcta es: 1,1-dibromo-3-phenylpropane
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