Organic Chemistry II Lab #3, Fall 2024 - PDF

***PARTNER NAMES: Zweede Lewis*** ***Sharon Makovore*** ***CHEM 225*** ***ORGANIC CHEMISTRY II LABORATORY*** ***LABORATORY \#3, FALL 2024*** ***Reactions of alcohols and Phenol*** ***COURSE DIRECTOR: Tobias Clement*** ***Instructors: Candice Benjamin, Tobias Clement, Reeba Lewis*** +--------...

***PARTNER NAMES: Zweede Lewis*** ***Sharon Makovore*** ***CHEM 225*** ***ORGANIC CHEMISTRY II LABORATORY*** ***LABORATORY \#3, FALL 2024*** ***Reactions of alcohols and Phenol*** ***COURSE DIRECTOR: Tobias Clement*** ***Instructors: Candice Benjamin, Tobias Clement, Reeba Lewis*** +-----------------------+-----------------------+-----------------------+ | **Tests ( 2 points)** | **Observation** | **Inference** | +=======================+=======================+=======================+ | **a) Solubility** | A\) no change on the | A\) For Alcohol A, | | | addition of H2O | there was no | | i). Test the | | observable change, | | solubility of | Red litmus - no | resulting in a | | alcohol, by taking | change | homogeneous, | | about 1ml of alcohol | | colorless solution. | | in a test tube and | Blue litmus - no | This suggests that | | adding an equal | change | Alcohol A has a | | amount of water. | | lower molecular | | | Unknown: 2 distinct | weight and fewer | | ii). Dip litmus paper | layers formed on the | carbon atoms, which | | in the resulting | addition of H20 | enables it to mix | | solution and note any | | well with water. In | | change | Red Litmus - no | contrast, the | | | change | unknown alcohol | | | | produced two | | | Blue litmus - no | distinct colorless | | | change | layers, indicating | | | | that it likely has | | | | a higher molar mass | | | | and a greater | | | | number of carbon | | | | atoms. The presence | | | | of multiple carbon | | | | atoms may have | | | | contributed to the | | | | unknown alcohol\'s | | | | insolubility in | | | | water, overpowering | | | | the hydrophilic | | | | characteristics of | | | | the -OH group. | | | | | | | | ii\) Strong acids | | | | cause blue litmus | | | | paper to turn red, | | | | while strong bases | | | | turn red litmus | | | | paper blue. Since | | | | there was no change | | | | observed when both | | | | Alcohol A and the | | | | unknown alcohol | | | | were tested with | | | | litmus paper, it | | | | can be concluded | | | | that both | | | | substances are weak | | | | acids or bases. | +-----------------------+-----------------------+-----------------------+ +-----------------------+-----------------------+-----------------------+ | **Tests (1 point)** | **Observation** | **Inference** | +=======================+=======================+=======================+ | **b) Ignition** | A; ignited slowly | A\) The absence of | | | when introduced to a | residue suggests | | Place a about 1ml of | splint, small orange | that complete | | the alcohol in a | flame, burned | combustion has | | crucible and ignite | completely with no | taken place. | | | residue | | | **(*Write equation | | Unknown) The presence | | for combustion of | Unknown; ignited | of black or brown | | butanol*)** | quickly when | residue in the | | | introduced to lit | crucible indicates | | | splint, large orange | incomplete | | | flame, black smoke, | combustion, which | | | brown or black | happens when there is | | | residue remained in | insufficient oxygen | | | crucible, burned | available. | | | completely | | | | | | | | 2C4H10 (l) + 13O2 (g) | | | | 8 CO2 (g) + 10H2O (g) | | +-----------------------+-----------------------+-----------------------+ **(2 points)** +-----------------------+-----------------------+-----------------------+ | **Tests ( 2 | **Observation** | **Inference** | | points),** | | | +=======================+=======================+=======================+ | **c). | A\) no colour change | A. The presence of | | Esterification** | after water bath, | an acetone odor | | | nail polish remove | suggests that an | | To about 2 cm^3^ of | (acetone) smell | ester was formed | | alcohol, add about 1 | with the addition | after acetic acid | | cm^3^ of glacial | of H2O | was added to | | ethanoic acid | | sample A. | | followed by a few | Unknown) no colour | | | drops of concentrated | change after water | Unknown) The | | sulfuric acid. | bath, nail polish | acetone smell | | | remover smell with | indicates that an | | Heat the mixture in a | the addition of water | ester was | | water bath. | | produced, along | | | C2H5OH (l) + CH3COOH | with acetic acid | | Pour the resulting | (aq) | and the unknown | | mixture into water | | substance. | | and note the smell | CH3COO2H5(l) | | | | | | | Write equation for | | | | esterification of | | | | ethanol with ethanoic | | | | acid | | | +-----------------------+-----------------------+-----------------------+ +-----------------------+-----------------------+-----------------------+ | **Tests (1 point)** | **Observation** | **Inference** | +=======================+=======================+=======================+ | **d) Oxidation** | Addition of A; No | Only primary and | | | colour change | secondary alcohols | | To each of the four | | are capable of | | test tubes provided, | Addition of B; 2 | undergoing oxidation. | | add 2mls of a 1% | layers formed; a more | After introducing a | | sodium dichromate | orange top layer | 1% sodium dichromate | | solution and 5 drops | | solution, a strong | | of conc. Sulfuric | Addition of C; 2 | oxidizing agent, and | | acid and mix the | distinct layers | placing the mixture | | contents thoroughly. | formed; opaque top | in a water bath, a | | Add 10 drops of A in | layer | reaction was observed | | tube 1, 10 drops of B | | solely for samples A | | in tube 2, 10 drops | Addition of Unknown; | and B. This indicates | | of C in tube 3 and 10 | 2 distinct layers | that the alcohols | | drops of your unknown | formed; opaque top | labeled A and B are | | to the fourth tube. | layer | likely either primary | | | | or secondary | | Cork all 4 test tubes | After water bath | alcohols. In | | and warm gently in a | | contrast, the lack of | | 40 -- 50^o^C water | A\) dark green | reaction with the | | bath for a minute. | colour resulted | unknown alcohol when | | Observe and record | | exposed to the strong | | any color changes. | B\) colour changed | oxidizing agent | | | from dark green | suggests that it is a | | | separated on the | tertiary alcohol. | | | top, with a | | | | yellowish orange on | | | | the bottom | | | | | | | | (The after completely | | | | turned dark green | | | | after being shook) | | | | | | | | C\) changed to a | | | | bright yellowish | | | | colour | | | | | | | | (unknown) changed to | | | | a bright yellowish | | | | colour | | +-----------------------+-----------------------+-----------------------+ +-----------------------+-----------------------+-----------------------+ | **Tests (1 point)** | **Observation** | **Inference** | +=======================+=======================+=======================+ | **e) Triodomethane | Addition of NaOH | The formation of a | | (Iodoform) test** | | precipitate after the | | | A\) color change | bath indicates that | | Add about 5 cm^3^ | from brown to light | alcohol B is a | | each of iodine into | yellow | secondary alcohol | | two test tubes. Then | | containing a methyl | | add 5 drops of | B\) colour change | group, specifically | | ethanol to one tube | from dark brown to | ethanol, as it | | and 5 drops of | opaque yellow | produced a positive | | 2-methyl butan-2-ol | | iodoform test. In | | into the other. | After water bath | contrast, the absence | | | | of precipitate for | | Now add sodium | A\) color change to | alcohol A suggests | | hydroxide carefully | mostly clear with a | that it is either a | | until the iodine | yellow tinge | primary or tertiary | | color has almost | | alcohol, resulting in | | discharged and warm | B\) pale yellow | a negative iodoform | | the mixture in a | solution with | test. | | water bath for 2-3 | precipitate formed | | | minutes. (The | the bottom | | | temperature should | | | | not exceed 60°C). | Equation: | | | Cool the tube and | | | | note the crystals | 3CH3CH2OH + 8I2 + 12 | | | formed. | NaOH | | | | | | | **Write the equation | 3CHI3 + 12NaI + 9H2O | | | for the formation of | | | | CHI~3~ (Iodoform | | | | reaction)** | | | +-----------------------+-----------------------+-----------------------+ +-----------------------+-----------------------+-----------------------+ | **Tests (1 point)** | **Observation** | **Inference** | +=======================+=======================+=======================+ | **f) Solubility of | After being shaken: | Phenols exhibit | | phenol** | the color went from | slight solubility in | | | clear to cloudy | water. When heated, | | i).Take enough phenol | opaque white; turned | their solubility | | to cover the bottom | clear at 39.5 degrees | increases, allowing | | of a test tube and | C; turned red litmus | them to dissolve more | | add about 2 cm^3^ of | blue, blue litmus | readily. However, as | | water. Stopper the | remained the same | the solution cools, | | test tube and shake | | solubility decreases, | | to obtain an | | resulting in the | | emulsion. Remove the | | formation of a | | cork, place the test | | colloidal dispersion | | tube in a beaker of | | or emulsion. | | water and warm. Put a | | Additionally, the | | thermometer in the | | litmus test indicates | | phenol solution and | | that phenols possess | | note the temperature | | acidic properties. | | when the emulsion | | | | clears. ii). Test | | | | also the solution | | | | with litmus paper. | | | | Cool this solution | | | | and use for other | | | | tests | | | +-----------------------+-----------------------+-----------------------+ +-----------------------+-----------------------+-----------------------+ | **Tests (1 point)** | **Observation** | **Inference** | +=======================+=======================+=======================+ | **g) Sodium | 2 distinct layers | the reaction between | | hydroxide** | were formed; a | sodium hydroxide and | | | slighty cloudy opaque | phenols is an acid | | To 5 drops of aqueous | white top layer and | base reaction. Where | | phenol, add sodium | then a clear layer | the Phenol being | | hydroxide until a | | acidic and sodium | | clear solution is | | hydroxide being basic | | obtained. | | the resultant would | | | | be a salt Called | | Add a few drops of | | Sodium Phenoxide and | | concentrated | | water. The addition | | hydrochloric acid and | | of HCL will then | | note the reappearance | | cause a shift in the | | of Phenol | | reaction equilibrium | | | | to the left reactant | | | | side thus forming | | | | more phenols, | | | | ultimately decreasing | | | | the concentration of | | | | sodium Phenoxide. | | | | | | | | C6H5OH + NaOH = | | | | C6H5Na + H2O | | | | | | | | Through the addiction | | | | of HCL: | | | | | | | | C6H5Na + HCL = NaCL + | | | | C6H5OH | +-----------------------+-----------------------+-----------------------+ +-----------------------+-----------------------+-----------------------+ | **Tests (1 point)** | **Observation** | **Inference** | +=======================+=======================+=======================+ | **h) Iron (III) | opaque white color | the formation of the | | chloride** | turned violet; then | violet color | | | changed color to a | indicates the | | To a solution of | light transparent | presence of a phenol. | | phenol add 1 drop of | brown after being | The product, Ferric | | iron (III) chloride | shook | phenol (C6H5OFe12) | | | | was formed in the | | | | reaction. | +-----------------------+-----------------------+-----------------------+