Question

Alcohol Halogenation Procedure

1. Enter the synthesis lab [left-hand desk]. Click on Alcohol Halogenation on the chalkboard.
2. Decide on the appropriate starting reagent[s] to synthesize chlorocyclohexane. Use ether as solvent.
3. Build the experimental setup. Use a heater, condenser and nitrogen gas. Add the appropriate organic reagents to a flask, and move the flask to the stir plate. Add the inorganic reagent.
4. You will monitor the reaction on the chalkboard and with TLC. Since you'll be running two syntheses in this experiment, you'll need to organize your TLC plate results so that you know what result belongs to which compound, as you did in earlier experiments.
5. Run a TLC plate before you start the reaction, and save it. Some reactants may not show up on TLC so make sure that you check the contents of the reaction vessel on the chalkboard.
6. Note the time on the laboratory clock. Start the reaction by turning on the stir plate. Advance the laboratory clock by an interval of 1 minute and run another TLC plate and check the chalkboard. Save every TLC plate that you run.
7. Repeat this step until you note the appearance of product on the TLC plate or on the chalkboard. Note the time and calculate the time to the first appearance of product.
8. If no product has appeared by 10 minutes, then advance the clock by intervals of 10 minutes until product appears. Note the time.
9. Continue running TLC plates until there is no more starting reagent visible on the TLC plate and the starting reagent has disappeared from the chalkboard. Save your last TLC plate to your book.
10. Take screenshots of your TLC plates.
11. Clean up.
12. Repeat the procedure to synthesize 2-chloro-2-methylpropane.
13. In preparation for the assessment, summarize your results, answering the following questions for each synthesis:
    1. starting reagent name and structure
    2. classify starting compound as primary, secondary or tertiary alcohol
    3. compounds in flask at start of reaction for each synthesis
    4. time for reaction to go to completion   
    5. product name and structure

Rank the reactions from fastest to go to completion to slowest to go to completion. Have available your TLC plate screenshots. Also, please make sure to review the topic of alcohol halogenation, in your text or elsewhere.

In order to have access to the assessment, you will need to submit your starting and final TLC screenshots. Insert the screenshots into a single word-processor document, and then label them in the document so that your instructor can tell what compound they represent, and which is the starting and which the final TLC. Then upload the final containing the screenshots into the assignment link below, and submit it. Upon submission, the assessment will become available.

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