Experiment 8: Nucleophilic Substitution Reactions of Alkyl Halides

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1 Experiment 8: Nucleophilic Substitution Reactions of Alkyl Halides exp 1: Reaction with Sodium Iodide in Acetone exp 2: Reaction with Silver Nitrate in Ethanol Reading: Carey & Guiliano Ch. 8 pgs

2 Nucleophilic Substitution Important reaction of alkyl halides Two common mechanistic pathways: S N 1: substitution, nucleophilic, unimolecular RDS S N 2: substitution, nucleophilic, bimolecular RDS

3 Reaction Features S N 1 Reactions: - rate determining step involves ionizaton carbocation - reaction rate governed by cation stability - RX: 3 > 2 >> 1 S N 2 Reactions: - rate determining step involves backside attack of Nu - reaction rate governed by sterics - RX: 1 > 2 >> 3

4 Comparison: S N 1 vs. S N 2 S N 1 S N 2 intermediate mechanism kinetics nucleophile solvent rate determined by substrate stereochemistry rearrangements carbocation stepwise 1st order weak or strong polar, protic cation stability 3 > 2 > 1 retention & inversion common no formal intermediate concerted 2nd order strong various sterics CH 3 X > 1 > 2 > 3 inversion not possible

5 Next Week (November 7-11) Experiment 8: Nucleophilic Substitution Reactions of R-X A. NaI in Acetone reaction via S N 2 mechanism B. AgNO 3 in ethanol reaction via S N 1 mechanism NOTE: We will not do concentration studies for either part DUE: Alkyne Synthesis Lab Report (exp 7) Lab Reports are due at the beginning of your regular lab session

6 Substrates

7 Reactions NaI in acetone (S N 2) - I - is a very good nucleophile - acetone is a polar, aprotic solvent - reaction will result in precipitate formation (NaCl or NaBr) AgNO 3 in ethanol or ethanol/water (S N 1) - Ag + in protic solvent - rapidly generates R + and AgX (ppt) formation of ppt tells you reaction has occurred - subsequent reaction of R + with solvent (ethanol), etc.

8 Determine Characteristics of Nu Substitution Evaluate the reactivity of the alkyl halide substrates considering: - primary structure (1, 2, 3 ) - secondary structure (steric effects, proximity of double bonds) - nature of the leaving group (Br vs Cl) - concentration (substrate vs. reagent) - should understand - solvent (S N 1 vs S N 2 reaction) - reaction temperature (will evaluate indirectly) Qualitative evaluation - be ready to observe and record your results - watch for ppt formation - no products will be isolated - no yield will be determined

9 Experimental Details - NaI in acetone (S N 2) 1. Obtain microtubes & corks (8-10 each) - be sure tubes are clean & dry 2. Add 15% NaI/acetone (2 ml) to reaction tubes - more is not better 3. Add substrates to reaction tubes - 2 drops of substrate per reaction tube (~ 0.1 ml) - one substrate per tube - be sure to label them so you know what is in each one! - immediately stopper tubes, mix thoroughly, note start time - watch for ppt formation at room temperature record the exact time for ppt formation (if any) in each tube try to quantify how much ppt forms (a lot? just a little?) also record observations when no ppt forms 4. If no precipitate forms after ~ 5 minutes, heat to 50 C in hot water bath - note start time - watch for reaction (ppt formation) over next 4-5 minutes - record observations (e.g. reaction time; quantity of precipitate)

10 Experimental Details - NaI in acetone (S N 2) Specific Experiments: 1. Primary Structure - substrates: - expectations?: 1 > 2 >> 3 >>>> aryl 2. Secondary Structure - substrates: - expectations?: allylic > 1 unhindered > hindered

11 Experimental Details - NaI in acetone (S N 2) Specific Experiments (cont): 3. Leaving Group - substrates: - expectations?: Br > Cl (Br better able to accommodate negative charge) 4. Concentration (NOTE: we will not do this portion of the experiment) - substrate: - variations: change substrate concentration change Nu concentration - expectations?: both situations will result in an increase in reaction rate specifically, expect rate to double in each case because the reaction is bimolecular! k = [RX][I - ]

12 Experimental Details - AgNO 3 in ethanol (S N 1) 1. Empty microtubes from last set of reactions & wash with ethanol - DO NOT use acetone! 2. Add 1% AgNO 3 /ethanol (1 ml) to reaction tubes - more is not better 3. Add substrates to reaction tubes - 2 drops of substrate per reaction tube (~ 0.1 ml) - one substrate per tube (be sure you know what's in each one!) - immediately stopper tubes, mix thoroughly, note start time - watch for ppt formation at room temperature record the exact time for ppt formation (if any) in each tube try to quantify how much ppt forms (a lot? just a little?) also record observations when no ppt forms 4. If no precipitate forms after ~ 5 minutes, heat to 50 C in hot water bath - note start time - record observations as before 5. When finished, wash tubes (rinse well!), dry, & return - PLEASE do not put them in your drawer!

13 Experimental Details - AgNO 3 in ethanol (S N 1) Specific Experiments: 1. Primary Structure - substrates: - expectations?: 3 > 2 >> 1 >>>> aryl 2. Secondary Structure - substrates: - expectations?: allylic > 1 why??

14 Experimental Details - AgNO 3 in ethanol (S N 1) Specific Experiments (cont): 3. Leaving Group - substrates: - expectations?: Br > Cl (Br better able to accommodate negative charge) 4. Concentration (NOTE: we will not do this portion of the experiment) - substrate: - variations: double substrate concentration double Nu concentration - expectations?: double [RX], expect reaction rate to double double [Nu], expect no change because the reaction is unimolecular! k = [RX]

15 Experimental Details - AgNO 3 in ethanol (S N 1) Specific Experiments (cont): 5. Solvent - substrate: - variations: ethanol ethanol/water - expectations?: rxn in ethanol/water will be faster both are polar, protic solvents (favor S N 1) pure water has a higher dielectric constant = more polar (really favors S N 1)

16 Writing the Lab Report: Exp #8 Alkyne Synthesis Purpose - what will you make? - include a balanced chemical equation for every reaction you did Results & Discussion - Comment on the success of your reaction sequence Did each step work? How do you know? physical appearance, TLC & melting point don t forget to discuss the changes in Rf values that you observe - Were the products pure? How do you know? TLC & mp data Was your recrystallization successful for step 2? - Was the reaction sequence efficient? Calculate the % yield for each step Calculate the overall yield

17 Writing the Lab Report: Exp #8 Alkyne Synthesis Conclusion - a brief recap of your findings - was your reaction sequence successful (did you make it? was it pure?) - do not include theory Appendix A: Calculations - Table of reagents (for each step) - Determine the limiting reagent (for each step) - Percent Yield calculation (for each step) for step 2, keep in mind you may not have recrystallized everything see page 91 of the lab manual for details - Overall Yield calculation example follows - Rf calculation Appendix B: Spectra - none

18 Calculating Overall Yield: Reaction Sequence: 1. Calculate yield for each step (as discussed last week) 87% 94% 2. Multiply individual yields together Overall Yield = (yield step 1 ) x (yield step 2 )... x 100 = (0.87) x (0.94) x 100 = 82%

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