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Dehydration of 1-Octanol to form 1-octene: Addition Reactions - Prof. Grady G. Sceals, Study notes of Fish Farming

TEST BANK Physical Examination and Health Assessment 9th Edition by Carolyn Jarvis,

Typology: Study notes

2022/2023

Uploaded on 09/04/2024

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Chem.2302K Fall 2020
Gh.Mandouma Lab 2: Dehydration of 1-Octanol to form 1-octene: Addition Reactions
Lab Report Due: Friday 10/09/2020 (NO EXTENSION ALLOWED)
Graphical Abstract:
Purpose:
Dehydration 1-octanol to afford 1-octene is done at moderate temperature under catalytic condition
(phosphoric acid).
1-octanol has a higher boiling point (bp. 161 °C) than water and/or 1-octene (bp. 83 °C). The latter can
therefore be distilled off (albeit with some water) the reaction mixture via a fractionating column
attached to the reaction mixture. To fully recover the distilling 1-octene that may be trapped inside the
column, aluminum foil must be used to wrap around the Vigreux fractionating column as well as the
distilling head to keep them warm enough, and the distilling compound will keep flowing. Furthermore
one must then separate 1-octene from residual water in a clean and dry separatory funnel and by
further drying the organic compound with a convenient drying agent (anhydrous calcium chloride
pellets) for 10-15 min. Filtering off the drying reagent will provide 1-octene for the subsequent bromine
test and additional reactions as outlined below.
Materials:
-1-octanol
- Phosphoric acid concentrated: 5 mL
- 100-mL round-bottomed flask equipped with one boiling stone
- A fractionating or Vigreux distillation column (must be handled with great care, yet without
fear!) topped with a distillation head (short column)
- Anhydrous calcium chloride (drying agent) to be measured only when needed (2 spatula/scoops)
- A thermometer and the appropriate glass/rubber adapter topping the short column
- A condenser with hoses to allow water in (bottom) and out (top)
- An elbow glass adapter dipping into a test tube cooled in a 125-mL Erlenmeyer flask
- A separatory funnel with a glass stopper
- 4 test tubes labelled A, B, C, D and 4 clean matching-size plain (i.e. no hole) corks
- A heating mantle/regulator
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Chem.2302K Fall 2020 Gh.Mandouma Lab 2: Dehydration of 1-Octanol to form 1-octene: Addition Reactions Lab Report Due: Friday 10/09/2020 (NO EXTENSION ALLOWED) Graphical Abstract: Purpose : Dehydration 1-octanol to afford 1-octene is done at moderate temperature under catalytic condition (phosphoric acid). 1-octanol has a higher boiling point (bp. 161 °C) than water and/or 1-octene (bp. 83 °C). The latter can therefore be distilled off (albeit with some water) the reaction mixture via a fractionating column attached to the reaction mixture. To fully recover the distilling 1-octene that may be trapped inside the column, aluminum foil must be used to wrap around the Vigreux fractionating column as well as the distilling head to keep them warm enough, and the distilling compound will keep flowing. Furthermore one must then separate 1-octene from residual water in a clean and dry separatory funnel and by further drying the organic compound with a convenient drying agent (anhydrous calcium chloride pellets) for 10-15 min. Filtering off the drying reagent will provide 1-octene for the subsequent bromine test and additional reactions as outlined below. Materials :

  • 1-octanol
  • Phosphoric acid concentrated: 5 mL
  • 100-mL round-bottomed flask equipped with one boiling stone
  • A fractionating or Vigreux distillation column (must be handled with great care, yet without fear!) topped with a distillation head (short column)
  • Anhydrous calcium chloride (drying agent) to be measured only when needed (2 spatula/scoops)
  • A thermometer and the appropriate glass/rubber adapter topping the short column
  • A condenser with hoses to allow water in (bottom) and out (top)
  • An elbow glass adapter dipping into a test tube cooled in a 125-mL Erlenmeyer flask
  • A separatory funnel with a glass stopper
  • 4 test tubes labelled A, B, C, D and 4 clean matching-size plain (i.e. no hole) corks
  • A heating mantle/regulator
  • Ice Methods : Add 20.0g of 1-octanol, 5 mL of concentrated phosphoric acid, and one boiling stone in a 100 mL round- bottomed flask, shaking to mix the layers. Observe/feel the heat of the reaction. Set up a fractional distillation by:
  1. Clamping the flask firmly to a stand before adding a Vigreux column (CAUTION! $100 fine for anybody who breaks this expensive piece of equipment), a distillation head, a thermometer via the glass/rubber adapter, a water-cooled condenser via the side arm of the distillation head, and an ice-water bath cooled test tube to receive the distillate;
  2. Checking with the instructor that your set up is fine TO PROCEED;
  3. Heat, observe the distillation ring rising up the Vigreuc column and distill the mixture until the residue in the flask is about 5-10 mL (when the flask is about to be dry); YOU MUST ALWAYS NOTE THE TEMPERATURE AND RECORD IT EVERY TWO MINUTES; To speed up distillation wrap the Vigreux column with alumina foil (CAUTION: if too hot, let the instructor do this for you) up to around the distilling head.
  4. Remove the heating mantle (and NOTHING else!) and let the reaction mixture cool as well as the set up to cool (5-10 min).
  5. Pour the distillate into a separatory funnel to separate the larger organic layer from residual water (if visible) into a clean and dry 25mL or 50mL erlenmeyer flask, and add two spatula-full of anhydrous calcium chloride and let it dry for 10 min.
  6. Filter off the drying agent (Regular filtration) and collect your organic layer into roughly equal amounts in test tubes A, B, C, D. Reactions of Alkenes: Bromination and Hydrobromination of 1-Octene Materials and Methods:
  • 1-octene:
  • Hydrobromic acid concentrated (caution: must be used under the hood) or conc. Hydrochloric acid can also be used: 5 mL dispensed dropwise to test tube A containing the alkene (1-octene); this test tube must be wrapped with alumina foil beforehand.
  • Solution of Bromine (any work with bromine must be done under the fume hood) in CHCl 3 is added dropwise to test tube B containing 1-octene;

PRE-LAB

Lab Safety Clearance Form (to be signed and submitted at the start of the lab technique)

- Students must read the experiment and the MSDS (Material Safety Data Sheet) for all the

chemicals to be used in this lab technique prior to entering the lab. It is mandatory for

everyone who may be exposed to potentially toxic liquid, solid, and/or gaseous

compounds to take every precaution needed based on the information pertaining to the

safety hazards of each compound, equipment and/or technique.

- Students must fill the Table of safety hazards for each compound used in this lab (listed

below or any replacement thereof when necessary):

# Name of

Substance/Technique/Equipment

Safety

Hazards

Potential and

Other

Concerns

Proper

Attire/Covering

Submitted by……………………………………………………. Date:…………………………...

Checked by ………………………………………………………Date:…………………………...