Please explain why! 1. Consider the substitution reaction that take place when(R
ID: 688704 • Letter: P
Question
Please explain why!1. Consider the substitution reaction that take place when(R)-3-bromo-3-methylhexane is treated with methanol. Which of thefollowing would be true?
A) The reaction would take place ONLY with inversion ofconfiguration at the stereogenic center.
B) The reaction would take place ONLY with retention ofconfiguration at the stereogenic center.
C) The reaction would take place with racemization.
D) No reaction would take place.
E) The alkyl halide does not possess a stereogenic center.
2. Consider the substitution reaction that takes place when(R)-3-bromo-3-methylhexane is treated with sodium methoxide. Whichof the following would be true?
A) An Sn2 reaction would take place with inversion of configurationat the stereogenic center.
B) An Sn1 reaction would take place with retention of configurationat the stereogenic center.
C) An Sn1 reaction would take place with racemization ofconfiguration at the stereogenic center.
D) An Sn1 reaction would take place, accompanied by an E1 reaction,affording a complex mixture of products.
E) An E2 reaction would take place, during which the stereogeniccenter is lost.
3. Consider the substitution reaction that takes place when(R)-3-iodo-3-methylheptane is treated with sodium acetate(CH3CO2Na). Which of the following would betrue?
A) An Sn2 reaction would take place with inversion of configurationat the stereogenic center.
B) An Sn1 reaction would take place with retention of configurationat the stereogenic center.
C) An Sn1 reaction would take place with racemization ofconfiguration at the stereogenic center.
D) An Sn1 reaction would take place, accompanied by an E1 reaction,affording a complex mixture of products.
E) An E2 reaction would take place, during which the stereogeniccenter is lost.
Explanation / Answer
1) C) The reaction would take place with racemization. (Methanol isa polar protic solvent, which is clue to the reaction occurring viaSn1. 3y halides also prefer elimination or Sn1,depending on the other reagents and conditions set) 2) E) An E2 reaction would take place, during which thestereogenic center is lost. (Sodium methoxide is a very strongbase, which is clue to the reaction being E2. 3y halidesalso prefer elimination or Sn1, depending on the other reagents andconditions set) 3) An Sn1 reaction would take place, accompanied by an E1reaction, affording a complex mixture of products. (The alkylhalide is 3y, Sn2 is not an option. Sodiumacetate is a weak base, which is clue to the rxn being E1/Sn1)