Mass of benzyl alcohol: 0.4mL 1.04 g = 0.416 g CiH:CHOH 1mL Moles of nitric acid: Nitric acid 1.2mL Limiting Reagent: Benzyl alcohol 0.4 ml CH-CH-OH 1.04 g CatsCH₂OH 1 mL CH:CH₂OH 15.7 M = 18.84 mmol = 0.01884 mol HNDI 1L Theoretical Yield: 1mol CutsCOOH 108.14g CH-CH₂OH (0.003847 mol CH-COOH 0.01884 mol HNDs | 1 mol CH-COOH = 0.00471 mol CECOOH 4 mol HNOs 0.416g CH;CH:OH 1 mol Cal:CH:OH I mol Cl-COOH 122.128 CH-COOH = 0.47g CaCOOH 108.14g CultiCHOH 1mal CH-CH-OH 1mol CHCOOH

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Ochem... can you please check my work for this prelab (oxidation of an alcohol to a carboxylic acid) I've circled important info in the lab... One important note was to take into account the concentration of nitric acid (HNO3, 15.7 M) Other amounts being used are 0.4 mL of benzyl alcohol and 1.2 mL of concentrated nitric acid Thank you!
Reaction:
CH-CH₂OH + HNO
Half Reactions:
CHCH₂OH
H20 + CH-CH₂OH-> CHCOOH + 4H+ 4e
Overall Reaction:
CH-CH₂OH + 4HNO₂
CECOOH
Mass of benzyl alcohol:
Moles of nitric acid:
Nitric acid
CaHCOOH + NO₂
0.4mL 1.04g = 0.416 g CH-CH₂OH
1 mL
Theoretical Yield:
HNO
4e + 4H+ 4HNO-> 4NO₂ + 41.0
CusCOOH + 4NO₂ + 3H₂0
1.2mL 15.7 M = 18.84 mmal = 0.01884 mol HNO
1L
Limiting Reagent:
Benzyl alcohol 0.4 ml CH-CHOH 1.04 g CaH:CH-OH |Imol CHCOOH = 0.003847 mol CECOOH
1 mL CaH:CH₂OH 108.14g Cali:CH₂OH
NO₂
0.01884 mol HNO: 1 mol CaH:COOH = 0.00471 mol Cu-COOH
4 mol HNOs
0.416g CH:CH:OH| 1mol CH5CH2OH |1 mol Cl-COOH
108.14g CusCHOH 1mal CaH:CH₂OH
122.12 g CH-C
|122.12 g CH-COOH =0.478 C COOH
1mal CaHCOOH
Transcribed Image Text:Reaction: CH-CH₂OH + HNO Half Reactions: CHCH₂OH H20 + CH-CH₂OH-> CHCOOH + 4H+ 4e Overall Reaction: CH-CH₂OH + 4HNO₂ CECOOH Mass of benzyl alcohol: Moles of nitric acid: Nitric acid CaHCOOH + NO₂ 0.4mL 1.04g = 0.416 g CH-CH₂OH 1 mL Theoretical Yield: HNO 4e + 4H+ 4HNO-> 4NO₂ + 41.0 CusCOOH + 4NO₂ + 3H₂0 1.2mL 15.7 M = 18.84 mmal = 0.01884 mol HNO 1L Limiting Reagent: Benzyl alcohol 0.4 ml CH-CHOH 1.04 g CaH:CH-OH |Imol CHCOOH = 0.003847 mol CECOOH 1 mL CaH:CH₂OH 108.14g Cali:CH₂OH NO₂ 0.01884 mol HNO: 1 mol CaH:COOH = 0.00471 mol Cu-COOH 4 mol HNOs 0.416g CH:CH:OH| 1mol CH5CH2OH |1 mol Cl-COOH 108.14g CusCHOH 1mal CaH:CH₂OH 122.12 g CH-C |122.12 g CH-COOH =0.478 C COOH 1mal CaHCOOH
EXPERIMENT 18
PURPOSE:
OXIDATION OF AN ALCOHOL TO A CARBOXYLIC ACID
To prepare a carboxylic acid via the oxidation of a primary alcohol. To demonstrate
methods of reaction, purification and spectroscopic analysis.
READ ABOUT: balancing redox equations, alcohol oxidation, microscale reactions.
EQUIPMENT: 5 mL reaction vial, microcondenser, Claisen adapter, drying tube, Hirsch
funnel/vacuum flask, hot plate, Al heating block
CHEMICALS: benzyl alcohol, concentrated nitric acid (HNO3, 15.7 M).
HAZARDS: Nitric acid is highly corrosive and an oxidizer. Avoid contact with skin and wash
immediately if it occurs.
DISCUSSION: Primary alcohols can oxidized to aldehydes or carboxylic acids depending upon the
reagent used. A gentle oxidizer such a cupric oxide (CuO) or pyridinium chlorochromate
(PCC) will stop at the aldehyde. However the more common oxidizing agents, such as chromic
acid (CrO3) or permanganate (MnO4), tend to proceed on to the carboxylic acid. Moreover,
these reagents contain metals that may yield toxic by-products. In this exercise, a less common
oxidizer, HNO3, will be used to carry out the following reaction.
OH
-CH₂ + HNO3
0&OH
+ NO₂
Nitric acid, while highly corrosive, is relatively easy to handle, and the product nitrogen oxides
(here represented by NO2) can be easily absorbed by base.
PRE-LAB:
In addition to the usual items, pre-lab preparation for this experiment should include the
following:
a) Write balanced equations for both half-reactions of the redox. Combine them
to determine the overall balanced redox equation.
b) Determine the limiting reagent and calculate the theoretical yield of acid.
Remember to take into account the concentration of the nitric acid solution.
PROCEDURE:
1) Assemble the reaction vial, Claisen adapter, and condenser as in Figure 12. Close the cap over the
straight side of the Claisen tube with a septum, Teflon side down.
2) Loosely fill the drying tube with glass wool. Moisten the glass wool with 10% NaOH solution
(approx. 10-20 drops). Attach the drying tube to the apparatus. This will act as a gas trap to
absorb nitrogen oxides produced.
3) Set up a hot plate with Al block and warm the block to 95-100°C. A setting of 4 may be used for
faster warming, but 2 should be sufficient to maintain the desired temperature.
70
4) Carefully measure 0.4 mL of benzyl alcohol
into the reaction vial. Connect to the
apparatus and place in the Al block to
warm. Initiate water flow in the
condenser.
5) Fill a syringe with 1.2 mL of concentrated
nitric acid and carefully insert the needle
through the septum, as shown in the
figure.
drying tube
E6335
loosely
moiste
condens
Transcribed Image Text:EXPERIMENT 18 PURPOSE: OXIDATION OF AN ALCOHOL TO A CARBOXYLIC ACID To prepare a carboxylic acid via the oxidation of a primary alcohol. To demonstrate methods of reaction, purification and spectroscopic analysis. READ ABOUT: balancing redox equations, alcohol oxidation, microscale reactions. EQUIPMENT: 5 mL reaction vial, microcondenser, Claisen adapter, drying tube, Hirsch funnel/vacuum flask, hot plate, Al heating block CHEMICALS: benzyl alcohol, concentrated nitric acid (HNO3, 15.7 M). HAZARDS: Nitric acid is highly corrosive and an oxidizer. Avoid contact with skin and wash immediately if it occurs. DISCUSSION: Primary alcohols can oxidized to aldehydes or carboxylic acids depending upon the reagent used. A gentle oxidizer such a cupric oxide (CuO) or pyridinium chlorochromate (PCC) will stop at the aldehyde. However the more common oxidizing agents, such as chromic acid (CrO3) or permanganate (MnO4), tend to proceed on to the carboxylic acid. Moreover, these reagents contain metals that may yield toxic by-products. In this exercise, a less common oxidizer, HNO3, will be used to carry out the following reaction. OH -CH₂ + HNO3 0&OH + NO₂ Nitric acid, while highly corrosive, is relatively easy to handle, and the product nitrogen oxides (here represented by NO2) can be easily absorbed by base. PRE-LAB: In addition to the usual items, pre-lab preparation for this experiment should include the following: a) Write balanced equations for both half-reactions of the redox. Combine them to determine the overall balanced redox equation. b) Determine the limiting reagent and calculate the theoretical yield of acid. Remember to take into account the concentration of the nitric acid solution. PROCEDURE: 1) Assemble the reaction vial, Claisen adapter, and condenser as in Figure 12. Close the cap over the straight side of the Claisen tube with a septum, Teflon side down. 2) Loosely fill the drying tube with glass wool. Moisten the glass wool with 10% NaOH solution (approx. 10-20 drops). Attach the drying tube to the apparatus. This will act as a gas trap to absorb nitrogen oxides produced. 3) Set up a hot plate with Al block and warm the block to 95-100°C. A setting of 4 may be used for faster warming, but 2 should be sufficient to maintain the desired temperature. 70 4) Carefully measure 0.4 mL of benzyl alcohol into the reaction vial. Connect to the apparatus and place in the Al block to warm. Initiate water flow in the condenser. 5) Fill a syringe with 1.2 mL of concentrated nitric acid and carefully insert the needle through the septum, as shown in the figure. drying tube E6335 loosely moiste condens
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