Synthesis of T-Pentyl Chloride

Better Essays
Exp 23 B
Synthesis of t-Pentyl Chloride

11-8-12

Purpose: The sysnthesis of t-Pentyl Chloride from alcohol.
Procedure:
Preparation of t-Pentyl Chloride. In a 125-mL separatory funnel, place 10.0 mL of t-pentyl alcohol (2-methyl-2-butanol, MW _ 88.2, d _ 0.805 g/mL) and 25 mL of concentrated hydrochloric acid (d _ 1.18 g/mL). Do not stopper the funnel. Gently swirl the mixture in the separatory funnel for about 1 minute. After this period of swirling, stopper the separatory funnel and carefully invert it. Without shaking the separatory funnel, immediately open the stopcock to release the pressure. Close the stopcock, shake the funnel several times, and again release the pressure through the stopcock (see Technique 12, Section 12.4). Shake the funnel for 2_3 minutes, with occasional venting. Allow the mixture to stand in the separatory funnel until the two layers have completely separated. The t-pentyl chloride
(d _ 0.865 g/mL) should be the top layer, but be sure to verify this by adding a few dropsof water. The water should dissolve in the lower (aqueous) layer. Drain and discard the lower layer.
Extraction. The operations in this paragraph should be done as rapidly as possiblebecause the t-pentyl chloride is unstable in water and sodium bicarbonate solution. It is easily hydrolyzed back to the alcohol. In each of the following steps, the organic layer should be on top; however, you should add a few drops of water to make sure. Wash (swirl and shake) the organic layer with 10 mL of water. Separate the layers and discard the aqueous phase after making certain that the proper layer has been saved. Add a 10-mL portion of 5% aqueous sodium bicarbonate to the separatory funnel. Gently swirl the funnel (unstoppered) until the contents are thoroughly mixed. Stopper the funnel and carefully invert it. Release the excess pressure through the stopcock. Gently shake the separatory funnel, with frequent release of pressure. Following this, vigorously shake the



References: http://answers.yahoo.com/question/index?qid=20080911092315AAXRbXU http://answers.yahoo.com/question/index?qid=20090603175731AAvMEzf A Small Scale approach to organic laboratory techniques, 3rd edition. Pavia, Lampman

You May Also Find These Documents Helpful

  • Good Essays

    t-Pentyl Chloride is a compound that is created through an SN1 nucleophilic substitution reaction in addition with Hydrogen Chloride in order to isolate the product. A variety of procedural techniques were utilized during the experiment including extraction, washing liquids, drying liquids, gravity filtration, and simple distillation. When a single solute or compound is transferred between two different solutes, it is known as extraction. Another technique that was utilized was washing, in which…

    • 1007 Words
    • 5 Pages
    Good Essays
  • Powerful Essays

    Synthesis of t-Pentyl Chloride Introduction: Using SN1 reaction mechanism with hydrochloric acid, t-Pentyl alcohol was converted to t-Pentyl chloride in an acid catalyzed reaction. The reaction took place in a separatory funnel designed to separate immiscible liquids. The crude product was extracted by transferring a solute from one solvent to another. The process of washing the solutions by phase transfer was used in order to remove impurities from the main solvent layer. Finally, the crude…

    • 1041 Words
    • 5 Pages
    Powerful Essays
  • Satisfactory Essays

    Discussion/Conclusion In this experiment, t-pentyl chloride was synthesis by reacting concentrated hydrochloric acid using nucleophilic substitution sn1. In the substitution reaction the Hydrogen in HCl protonated the alcohol group in t-pentyl alcohol and turned it to a good leaving group (H2O). a tertiary carbon cation was formed. a nucleophilic attach of the negative Cl- attacked the carbon cation forming t-pentyl chloride [7]. As the reaction proceeded, extraction and distillation techniques…

    • 338 Words
    • 2 Pages
    Satisfactory Essays
  • Powerful Essays

    Nucleophilic Substitution | Synthesis of n-Butyl Bromide and t-Pentyl Chloride | | Jessica | [Pick the date] | Abstract The synthesis of the alkyl halide n-Butyl Bromide from alcohol is the foundation for the experiment. During the isolation of the n-butyl bromide, the crude product is washed with sulfuric acid, water, and sodium bicarbonate to remove any remaining acid or n-butyl alcohol. The primary alkyl halide halide n-butyl bromide is prepared by allowing n-butyl alcohol to react with…

    • 1598 Words
    • 7 Pages
    Powerful Essays
  • Better Essays

    Preparation of t-Butyl-Chloride March 8 & 15, 2012 Theory: Alkyl halides can be synthesized when alcohols react with hydrogen halides. An alkyl halide is a halogen-substituted alkane, and a hydrogen halide is a compound consisting of a hydrogen bonded to a halogen (H-X). Alkyl halides are classified as primary, secondary, or tertiary depending on the number of alkyl substituents directly attached to the carbon bearing the halogen atom. The purpose of this laboratory experiment was to prepare t-butyl-chloride…

    • 2032 Words
    • 9 Pages
    Better Essays
  • Good Essays

    “The Synthesis of Zinc Chloride”, what a peculiar name for a lab that does not even involve synthesis. Synthesis, by definition, is when two elements are combined in a chemical reaction,but that is not the case. In this lab we are combining zinc, an element, and hydrochloric acid, a compound, but combining a compound and an element is not synthesis, it is single replacement. We are taking zinc and hydrochloric acid and making zinc chloride and hydrogen, a single replacement, but what occurred during…

    • 718 Words
    • 3 Pages
    Good Essays
  • Satisfactory Essays

    Experiment 11.1 Conversion of t-Amyl Alcohol to t-Amyl Chloride Using HCL October 27, 2011 Purpose: Alkyl halides can be prepared from alcohols by reacting them with a hydrogen halide, HX (X = Cl, Br, or I). The mechanisms of acid-catalyzed substitution of alcohols are termed SN1 and SN2. The “S” stands for substitution, the “N” stands for nucleophilic, and the “1” or “2” stand for unimolecular or bimolecular. Secondary alcohols react with hydrogen halides by both SN1 and SN2…

    • 419 Words
    • 2 Pages
    Satisfactory Essays
  • Powerful Essays

    Sodium Chloride

    • 1718 Words
    • 7 Pages

    Sodium chloride, also known as salt, common salt, table salt, or halite, is an ionic compound with the formula NaCl. Sodium chloride is the salt most responsible for the salinity of the ocean and of the extracellular fluid of many multicellular organisms. As the major ingredient in edible salt, it is commonly used as a condiment and food preservative. [edit] Properties Thermal conductivity of pure NaCl as a function of temperature has a maximum of 2.03 W/(cm K) at 8 K and decreases to 0.069 at 314…

    • 1718 Words
    • 7 Pages
    Powerful Essays
  • Good Essays

    Acetyl Chloride

    • 371 Words
    • 2 Pages

    Acetyl chloride, CH3COCl, also known as ethanoyl chloride or acyl chloride, is an acid chloride derived from acetic acid. It belongs to the class of organic compounds called acyl halides. It is a colorless liquid. Acetyl chloride does not exist in nature, because contact with water would hydrolyze it into acetic acid and hydrogen chloride. In fact, if handled in open air it gives off white smoke owing to the hydrolysis from the moisture in the air. The "smoke" is actually small droplets of hydrochloric…

    • 371 Words
    • 2 Pages
    Good Essays
  • Good Essays

    Hydrated Chloride

    • 692 Words
    • 3 Pages

    Purpose: The purpose of this experiment is to determine the number of moles of water molecules of crystallization of a sample of hydrated Barium Chloride. This can be calculated using Gravimetric Analysis and to indirectly determine the percent composition of a hydrate by taking advantage of its chemical properties. Introduction: Gravimetric procedures are analytical methods in which the results are determined from the masses of starting materials and products. These methods…

    • 692 Words
    • 3 Pages
    Good Essays