Question

Draw the strcture of all substrates you will be using in this reaction and classify them as( primary, Secondary, and tertiary) aryl bezylic or some combination of these (such as primary bezylic). Identify the nucleophile, substrate, and leaving group in general equations for reactions 1 and 2

ORRAS sminilah you dimensions (R) or (S), and show their stereochemistry clearly. If your instructor reguests, obtain another set of atoms and connectors and use it to prepare isomers as well. R eal rolecular am different ways to you will apply ar structure sodel kit, and you uy isomers dels are the time different kind ds that hold the 1 with a number ding alom hus, ballser r holes arranged Reactivities of Alkyl Halides in Nucleophilic Substitution Reactions MINE Before You Begin: Draw the structures of all substrates you will be using in this reaction and classify them as 1º, 2º, 3º, aryl, benzylic, or some combina- tion of these (such as 1° benzylic). Identify the nucleophile, substrate, and leaving group in the general equations for reactions 1 and 2. e two holes and odels of the tror putting the of isomers s, using lerable amous In this minilab, you will compare the relative reactivities of different walkyl halides with two different reagents: sodium iodide in acetone and sil- Yer nitrate in ethanol. General equations for their reactions are 1 RX + Nalatone, RI + NaX (X - Clor Br) 2. RX + AgNO, + EtOH — ROE! + AgX + HNO3 Additional organic products, such as alkenes, may be formed in reaction 2.) For each reagent, the occurrence of a reaction is indicated by the forma- ton of a precipitate: sodium chloride or sodium bromide (which are insoluble in acetone) in reaction 1, and silver chloride or silver bromide in reaction 2. Your initial objective is to discover what kind of mecha- hism (Spl or SN2) is involved in the reactions of each reagent. Based on your conclusions, you will predict the relative reactivities of other substrates with the reagents and test your predictions. In order to ac- complish these objectives, you will have to think about the significance of your observations as you make them, so that your results from one set of reactivity measurements can lead to predictions about another set of measurements. uctor wille tors, including bonds United epresented by DIRECTIONS All of the alkyl bromides are foxis and have harmful yonore and me

Answer 1

DIFFERENT SUBSTRATE:

10 halide: Halogen 'X' is connected to 'C' which is connected to 1 more 'C' 20 halide: Halogen 'X' is connected to 'C' which is connected to 2 more 'C' 30 halide: Halogen 'X' is connected to 'C' which is connected to 3 more 'C' CH3 H3C H3C-CH2 CH—X H2C— C— X H₃C CH3 3° alkyl halide 10 alkyl halide 20 alkyl halide H₃C CH-X CH2 Benzylic 'C' is represented in BLUE 1° benzyl halide 2° benzyl halide 30 benzyl halide {Halogen sitting on Aromatic group) Aryl halide

Reaction 1:

RX + NaI ------------> (acetone) RI + NaX (X=Cl or Br)

Substrate: RX

Leaving group: X^- (X = Cl or Br)

Nucleophile: I^-

Solvent: Acetone

Reaction 2:

RX + AgNO₃ + EtOH -----> ROEt + AgX + HNO₃

Substrate: RX

Leaving group: X^-

Nucleophile: EtOH (neutral nucleophile)

AgNO₃ is used to trap ‘X^-’ coming out as AgX