Organic Chemistry

2. Rank the following compounds in order of increasing acidity (weakest to strongest).

Question 56 (0.0001 points) (5 marks) Hand write your answers to the questions below. Select the tickbox when you have completed this question. a. Label with asterisks (*) all of the stereocentres in the molecule shown above. (1 mark) b. How many stereoisomers are possible? (1 mark) c. Draw the structures of one pair of enantiomers for the above molecule. (Hint: You should draw two structures using wedge and dashed wedge bonds.) (3 marks)

Question 57 (0.0001 points) (3 marks) Hand write your answers to the questions below. Select the tickbox when you have completed this question. Draw the structure of the following compound: trans-2-bromocyclohexanol

4. Calculate the transition energies for (1) for all solvents using the absorption maxima values collected by groups A, B, C and D.

Objectives (1 pt): identify the overall goal of the lab and briefly mention the methods used in the experiment along with relevant minor goals.

Experiment 3: (Determination of the composition of an unknown mixture using extraction based on acid/base properties

Draw all pertinent structures or when applicable, the full reaction mechanism with arrow pushing and intermediates included. All collected and calculated data must be tabulated including spectroscopic data with bond analysis (standards and experimental, indicating the EXACT wavenumber and the corresponding bond) Calculations MUST NOT BE in a table, should be shown under the table, TYPED! Display all calculating methods and formulas and show limiting reagent, theoretical and % yield Label all data and images, include legend for spectra and tables. Include whichever is applicable for each experiment: -Collected data (starting amounts, and collected amounts) (in a table format) -Calculated data (in a table format) (all calculations must be shown under the table to earn credit) -Show and use proper calculation formulas, for mass, moles, density, etc. -Calculate and show Limiting reagent  -Calculate and show Theoretical Yield  -Calculate and show % Yield  -Spectroscopy data with bonds labeled (standards and experimental, in a table format)

a. Provide the chemical formula of the molecule. Note that there are hydrogen atoms as part of the formula but these are not shown in the drawing. b. The picture does not show lone pairs of electrons. Redraw the structure and indicate where all lone pairs are located. Include all hydrogen atoms in your drawing. Note that there are 42 valence electrons.

In your lab notebook, prepare the following (see lab notebook guide for details): 1. Write all procedures required for this experiment. Prepare it so that it can be used as a sole source of your experimental procedures. 2. Write detailed, reaction mechanism of acetanilide synthesis using aniline and acetic anhydride. Must include arrows, electron flow and lone pairs. 3. Write written table of chemicals that include physicochemical data for all chemicals used (see chapter 6). 4. Write the theoretical yield calculations for this reaction. 5. Calculate the volume of liquid reagents used in the experiment (from Table 1)

EXPERIMENT 5: NaBH4 Reduction of a Ketone Objective: The purpose of experiment 5 is to reduce a ketone to its alcohol using sodium borohydride.