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    Lab Rep Exp 4 Sko

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    Nurfariha Safar
    This laboratory report details the synthesis of tert-butyl chloride from tert-butyl alcohol through a nucleophilic substitution reaction using HCl. The percentage yield obtained was 13.5049%. The reaction proceeded through an S N1 mechanism since tertiary alcohols readily form alkyl halides with HX. Factors like vigorous shaking and separating layers carefully could have improved the yield. The objective of synthesizing tert-butyl chloride was achieved although the percentage yield was lower than expected ranges.

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    Lab Rep Exp 4 Sko

    Uploaded by

    Nurfariha Safar
    172 views5 pages
    This laboratory report details the synthesis of tert-butyl chloride from tert-butyl alcohol through a nucleophilic substitution reaction using HCl. The percentage yield obtained was 13.5049%. The reaction proceeded through an S N1 mechanism since tertiary alcohols readily form alkyl halides with HX. Factors like vigorous shaking and separating layers carefully could have improved the yield. The objective of synthesizing tert-butyl chloride was achieved although the percentage yield was lower than expected ranges.

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    This laboratory report details the synthesis of tert-butyl chloride from tert-butyl alcohol through a nucleophilic substitution reaction using HCl. The percentage yield obtained was 13.5049%. The reaction proceeded through an S N1 mechanism since tertiary alcohols readily form alkyl halides with HX. Factors like vigorous shaking and separating layers carefully could have improved the yield. The objective of synthesizing tert-butyl chloride was achieved although the percentage yield was lower than expected ranges.

    Copyright:

    © All Rights Reserved
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    172 views5 pages

    Lab Rep Exp 4 Sko

    Uploaded by

    Nurfariha Safar
    This laboratory report details the synthesis of tert-butyl chloride from tert-butyl alcohol through a nucleophilic substitution reaction using HCl. The percentage yield obtained was 13.5049%. The reaction proceeded through an S N1 mechanism since tertiary alcohols readily form alkyl halides with HX. Factors like vigorous shaking and separating layers carefully could have improved the yield. The objective of synthesizing tert-butyl chloride was achieved although the percentage yield was lower than expected ranges.

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    © All Rights Reserved
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    Download as docx, pdf, or txt
    of 5

    DEPARTMENT OF CHEMISTRY

    FACULTY OF SCIENCE AND MATHEMATICS


    UNIVERSITI PENDIDIKAN SULTAN IDRIS

    LABORATORY REPORT

    SKO 3023
    ORGANIC CHEMISTRY 1

    EXPERIMENT TITLE

    4
    SYNTHESIS OF TERT-BUTYL CHLORIDE

    NAME ID / MATRIC NO.

    NUR AINA ANIRA BINTI SAARI D20171078182

    FATIH NOR SAHARIAH BINTI ABDUL JALIL D20171078195

    FATTIN SUERAYA BINTI AB RAHMAN D20171078205

    NURFARIHA BINTI SAFAR D20171078209

    LECTURER DR. WAN MOHD NUZUL HAKIMI W SALLEH

    GROUP B
    NO. ITEMS MARKS
    DATE 5/11/2019
    LABORATORY 1. Introduction 3
    2. Procedure / Methods 1
    MK5
    3. Results / Worksheets 5
    4. Discussion 5
    5. Conclusion 2
    6. References 1
    7. Question / Answer (if any) 2
    8. Format 1
    TOTAL 20
    EXPERIMENT 4: SYNTHESIS OF TERT – BUTYL CHLORIDE

    OBJECTIVE

    1) To synthesize tert- butyl chloride

    INTRODUCTION

    Alkyl halide also called haloalkanes are class of compounds with a halogen atom bonded to

    sp3 – hybridized carbon atom. Halogen atom X is more electronegative than carbon atom

    making the C-X bond polar and alkyl halide molecules to be more polar than hydrocarbons.

    Alkyl halide are categorized into three, which are primary, secondary and tertiary depending

    on the number of alkyl substituents attached into carbon atom which the halogen bonded.

    Alkyl halide can be prepared from alcohol by reacting them with hydrogen halide .Tertiary

    alcohol react readily with HX alone to form alkyl halide. The purpose of this experiment is to

    synthesize t-butyl chloride through nucleophilic substitution reaction of t-butyl alcohol with

    HCl. This method employs the relative stability of carbocation intermediate formed and thus

    proceeds through Sn1 reaction mechanism.

    The distillation process makes use of difference in boiling points of impurities and desired

    substances. This show effectivity of hydrohalogenation of tertiary alcohols to produce tertiary

    alkyl halides.
    CALCULATION

    Weight of tert-butyl chloride = 1.0556 g

    Density of 2 –chloro-2-methylpropanol = 0.7809 g/cm3

    Weight = density × volume

    = 0.7809 g/cm3 × 10 cm3

    = 7.8090 g

    7.809 g
    No of mole ( CH3 )3COH =
    163.522 g

    = 0.0478 mol

    ( CH3)3COH (aq) + HCl (aq) (CH3)3CCl (aq) + H2O (l)

    1 mole ( CH3)3COH produces 1 mole (CH3)3CCl

    0.0478 mol ( CH3)3COH produces 0.0478 mole of (CH3)3CCl

    Theoretical weight of (CH3)3CCl = 0.0478 mol × 163.522 g/mol

    = 7.8164 g

    Percentage yield = (experimental value / theoretical value) × 100

    1.0556 g
    = × 100
    7.8164 g

    = 13.5049 %
    DISCUSSION

    This lab experiment aimed to produce alkyl halide by reacting the corresponding alcohol with

    a hydrogen halide. Since we are using tertiary butyl alcohol, tertiary butyl alcohol molecules

    only undergo SN2 mechanism. This is because tertiary alcohols react readily with HX alone to

    form alkyl halide while secondary and primary require catalyzation on the halohydrogenation

    reaction.

    SN1 mechanisms are unimolecular because its slow step is unimolecular. The reaction

    proposed involves an initial step where the tertbutyloxonium ion is formed by protonation.

    This ion then dissociates to a second intermediate a carbocation - an ion that contains a

    positively charged carbon. Since only one species, tert-butyloxonium ion, undergoes a

    chemical change in this step, the step is unimolecular. This is the rate-controlling step. The

    carbocation (tert-butylcation) being strongly electrophilic then reacts with the nucleophile
    chloride ion in a fast step originating the tert-butyl chloride final product Since the

    nucleophile is not involved in the rate–determining step of the process a strong nucleophile is

    not important in this process.

    More stable carbocations are formed faster than the less stable ones. That stability is

    conferred by hyperconjugation - electron delocalization via orbital overlap. Therefore the

    SN1 mechanism is generally accepted to be correct for the reaction of tertiary and secondary

    alcohols with hydrogen halides but not for methyl and primary alcohols as methyl and

    primary carbocations are too unstable to be reasonably involved.

    From experiment, theoretical yield of tert-butyl chloride is 13.51% compared to theorical

    value for yields that are vary between 40% and 65%. This might caused by some error.

    Firstly, the vigorous shaking of the funnel might not enough since one of the factor to

    produce good yield is vigorous shaking or stirring. Second error might happen when we were

    separating layer of acid and raw tert-butyl chloride. Precaution need to be taken in this

    experiment is the stopper need to be press tightly before start shaking since the pressure

    inside the funnel is high and the stopper might bounce.

    CONCLUSION

    Tert-butyl chloride is synthesized with percentage yield of 13.5049 %.

    REFERENCES

    Organic Syntheses, Inc., (2019), A publication of reliable methods for the preparation of
    organic compounds, http://www.orgsyn.org/demo.aspx?prep=CV1P0144

    Master Organic Chemistry LLC, (2019), Primary,secondary, tertiary, quartenary in organic


    chemistry, https://www.masterorganicchemistry.com/2010/06/16/1-2-3-4/amp/

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