Reactivity of Alkyl Halides
a. Which test was overall faster? Give a rationale for why that test is faster. Use one of the substrates to help you explain, drawing an energy diagram might help as well.
b.For the AgNO3 test: Which substrate was fastest and which was slowest. Why? Draw a mechanism and energy diagram to help you explain these results.
Data Table
Test Tube # |
Reaction Time NaI test |
Reaction Time AgNo3 test |
||
1 2-chlorobutane |
00:03.25 |
No reaction |
||
2 2-bromobutane |
00:01.83 |
00:01.40 |
||
3 1-chlorobutane |
00:01.93 |
00:04.89 |
||
4 1-bromobutane |
00:02.70 |
00:05.02 |
||
5 2-chloro-2-butene |
00:01.00 |
00:03.46 |
||
6 benzyl chloride |
00:01.00 |
00:03.80 |
||
7 bromobenzene |
00:00.99 |
00:01.21 |
||
8 bromocyclopentane |
00:00.73 |
00:02.09 |
||
9 bromocyclohexane |
00:02.22 |
00:02.21 |
||
10 2-chloro-2- methylpropane |
00:00.65 |
00:01.78 |
Reactivity of Alkyl Halides a. Which test was overall faster? Give a rationale for why that...
Please HELP!! Table 1: Alkyl Halides in NaI Substrate Time for Precipitate to Form Heated? Temp (℃) Time (min) Heat Relative Ranking (#1-#6) Predicted Relative Ranking (#1-#6) Bromobenzene No reaction Yes 44 10 6 6 2-Chlorobutane No reaction Yes 44 10 5 4 1-Chlorobutane 13 min Yes 44 8 4 3 Benzyl Chloride 2min 30 sec No --- --- 2 1 1-Chloro-2-butene 1 second No --- --- 1 5 1-Bromobutane 5 min No --- --- 3 2 1. Why did...
1. Compare the reactivity of primary alkyl halides in part 1 (SN2) of this experiment to the reactivity of primary alkyl halides today. What conclusions, if any, can you make about the reactivity of these molecules under these different conditions? Use specific data to make your point. 2. Compare the reactivity of secondary alkyl halides in part 1 (SN2) of this experiment to the reactivity of secondary alkyl halides today. What conclusions, if any, can you make about the reactivity...
Relative ranking (#1 - #7) Reason for ranking 1-chlorobutane 1-chloro-2-butene 2-chlorobutane 1-bromobutane 2-chloro-2-methylpropane bromobenzene benzyl chloride (2) What mechanism do you believe will be favored with AgNO3 in ethanol? What order of reactivity do you predict will be observed when each of the alkyl halides in Figure 1is reacted with AgNOs in ethanol? Complete a similar table as in question #1 for these reaction conditions. Write your prediction of the mechanism and the order of reactivity with AGNO3 in ethanol...
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For the Reactions that formed precipitates, what are the drawn out reaction equations with stereochemistry if applicable? Part 1. Enter the results of each test into the table below: 1°, 2° or 3°? Alkyl Halides 1-chlorobutane Sn2 (Nal/acetone) Precipitate formed 1-bromobutane Precipitate formed 2-chlorobutane No precipitate formed 2-bromobutane No precipitate formed bromocyclohexane No precipitate formed 2-chloro-2-methylpropane (t-butyl chloride) No precipitate formed Crotyl chloride No precipitate formed Benzyl chloride (a-chlorotoluene) No precipitate formed Arrange the alkyl halides in order of reactivity...
2-chlorobutane 2-bromobutane 1-chlorobutane 1-bromobutane 2-chloro-2-methyl-propane Allyl chloride Benzyl Chloride Bromobenzene Bromocyclohexane Bromocyclopentane 1. Which substrates should be "very reactive" in SN2 reactions? 2. Which substrates should be "very reactive" in SN1 reactions?
Draw the reaction equation for the Sodium Iodide/Acetone test (SN2 mechanism) for each of the substances: 1. 1-chlorobutane 2. 2-chlorobutane 3. 2-chloro-2-methylpropane 4. 1-bromobutane 5. 2-bromobutane 6. benzyl chloride 7. bromocyclohexane 8. bromocyclopentane
In this exercise, you will use two reagent mixtures to test a variety of organic halides. The distinct differences in the factors affecting the SN2 and SN1 mechanisms make it possible to determine which mechanism is favored by a given compound. One reagent and solvent favors SN2 reactivity, the other SN1 reactivity. From the results of your tests, you will determine which mechanism, if either, is favored by a given compound. In your post-lab assignment, you will be required to...
(1) What mechanism do you believe will be favored with Nal in acetone? What order of reactivity do you predict will be observed when each of the alkyl halides in Figure 1 is reacted with Nal in acetone? Complete the below table; list the relative ranking of the reactivity of the alkyl halides and your reason for placing that alkyl halide at that ranking. Write your prediction of the mechanism and the order of reactivity with Nal in acetone as...
Arrange the alkyl halides in order of reactivity (from most to least reactive) under both SN1 (silver nitrate/ethanol) and SN2 (sodium iodide/acetone) conditions: 1-bromobutane, 2-bromobutane, bromocyclohexane, 2-bromo-2-methylpropane, 1-bromoadamantane, benzyl bromide, and bromobrmzene.