Answer the two multiple choice exam questions

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Elimination Reactions

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Substitution and Elimination

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Answer the two multiple choice exam questions 4/9/2019 Do Now: Answer the two multiple choice exam questions Y Z

MWB Show the mechanism between bromoethane and sodium hydroxide in cold, aqueous solution

Nucleophilic Substitution

What is meant by ‘rate-determining’ step?

The SN2 mechanism S = substitution N = nucleophilic 2 = bimolecular and second order Bimolecular – two species involved in the rate-determining step

Example

The SN2 mechanism Notice the arrangement of the three groups that remain attached to the central carbon has been inverted. Due to the inversion, the optical activity of the product is different from that of the reactant. If the reactant is dextrorotatory, then the product will be laevorotary. By measuring the optical activity of the original halogenoalkane and the alcohol formed, we can show whether it has occurred by the SN2 mechanism.

Question 2-chloropentane and hydroxide ions react together by an SN2 mechanism. Show the formation of 2-hydroxypentane. 2-bromobutane and cyanide ions react together by an SN2 mechanism. Draw the structure of the transition state formed in this reaction.

The SN1 mechanism S = substitution N = nucleophilic 1 = unimolecular and first order Unimolecular – only one species is involved in the rate-determining step

The SN1 mechanism Original halogenoalkane has a tetrahedral shape Product of the first step of the reaction is a carbocation with a planar shape Therefore there is an equal chance of the attacking nucleophile approaching from the left and the right Two enantiomer products are made Made in equal numbers, so a racemic mixture is formed./

Question 2-bromobutane and cyanide ions react together by an SN2 mechanism. Explain why there is no change in optical activity in this reaction.

SN1 or SN2? SN1 – tertiary halogenoalkanes SN2 – primary halogenoalkanes