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    Kelas Xiii Semester Gasal: Elusidasi Struktur Senyawa Organik Mata Diklat: Kimia Organik

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    1) The document describes procedures for determining the structure of organic compounds using spectroscopic data such as IR, NMR, and MS. 2) An example is given of determining the structure of a compound with Mr=60.0977. Using IR and NMR data, the structure is identified as 2-propanol, CH3CH(OH)CH3. 3) A second example of a compound with Mr=102.1360 is determined to be methyl butyrate, CH3CH2CH2COOCH3, by analyzing its IR and NMR spectra.

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    Kelas Xiii Semester Gasal: Elusidasi Struktur Senyawa Organik Mata Diklat: Kimia Organik

    Uploaded by

    Lutphia
    41 views12 pages
    1) The document describes procedures for determining the structure of organic compounds using spectroscopic data such as IR, NMR, and MS. 2) An example is given of determining the structure of a compound with Mr=60.0977. Using IR and NMR data, the structure is identified as 2-propanol, CH3CH(OH)CH3. 3) A second example of a compound with Mr=102.1360 is determined to be methyl butyrate, CH3CH2CH2COOCH3, by analyzing its IR and NMR spectra.

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    1. PRESENTASI 2.pptx

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    1) The document describes procedures for determining the structure of organic compounds using spectroscopic data such as IR, NMR, and MS. 2) An example is given of determining the structure of a compound with Mr=60.0977. Using IR and NMR data, the structure is identified as 2-propanol, CH3CH(OH)CH3. 3) A second example of a compound with Mr=102.1360 is determined to be methyl butyrate, CH3CH2CH2COOCH3, by analyzing its IR and NMR spectra.

    Copyright:

    © All Rights Reserved
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    Download as pptx, pdf, or txt
    41 views12 pages

    Kelas Xiii Semester Gasal: Elusidasi Struktur Senyawa Organik Mata Diklat: Kimia Organik

    Uploaded by

    Lutphia
    1) The document describes procedures for determining the structure of organic compounds using spectroscopic data such as IR, NMR, and MS. 2) An example is given of determining the structure of a compound with Mr=60.0977. Using IR and NMR data, the structure is identified as 2-propanol, CH3CH(OH)CH3. 3) A second example of a compound with Mr=102.1360 is determined to be methyl butyrate, CH3CH2CH2COOCH3, by analyzing its IR and NMR spectra.

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    © All Rights Reserved
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    Download as pptx, pdf, or txt
    of 12

    ELUSIDASI STRUKTUR SENYAWA

    ORGANIK
    MATA DIKLAT : KIMIA ORGANIK

    KELAS XIII
    SEMESTER GASAL

    DISUSUN OLEH :
    GINA LIBRIA N., S.Si., M.T

    KEMENTERIAN PERINDUSTRIAN R.I


    PUSAT PENDIDIKAN DAN PELATIHAN INDUSTRI
    SEKOLAH MENENGAH KEJURUAN – SMAK BOGOR
    2017
    1
    PROCEDURE TO DETERMINE STRUCTURE OF ORGANIC
    COMPOUND
    Procedure:
    1. Obtain the Mr and use it to look up the molecular formula.

    2.Rule out functional groups that cannot belong to the molecular formula.

    3. Examine the IR spectrum to determine the presence of suspected functional groups. This is
    done by examining the peaks in the functional group region (4000 - 1100cm-1) for peaks in
    positions that are characteristic of functional groups that can fit with the molecular formula.

    4.List the (main) possible isomeric structures.


    PROCEDURE TO DETERMINE STRUCTURE OF ORGANIC
    COMPOUND (2)

    5. Examine the NMR spectrum and note the number of peak groups and their integrals. This may indicate
    the number of methyl (CH3), methylene (CH2) and methine (CH) groups.

    6. Examine the NMR spectrum chemical shifts and attempt to determine the proximities of nearby
    protons to the functional group. If a functional group proton is suspected, it may be possible to locate it
    by consideration of the integral and chemical shift data.

    7. Examine the NMR spectrum for peak multiplicity in order to determine the number of protons on
    neighbouring groups. This will give the proton sequence that determines which isomer is the correct
    structure.

    8. Confirm the structure by checking the MS fragmentation pattern.


    EXAMPLE

    Example No. 1: Mr = 60.0977

    Example No. 1: Mr = 60.0977


    NMR SPECTRA
    HOW TO INTERPRETE:

    Working out:
    Mr = 60.0977 means that the molecular formula is C3H8O.
    The molecular formula rules out the possiblity of a carboxylic acid or amine.
    (Also - must not contain a carbonyl group or multiple C-C bonds, to accommodate all eight Hs
    in the structure)

    IR Strong and fairly broad absorption from 2800 to 3300 cm-1


    Hence, probably an alcohol (H-bonded in solution).
    Sharp peak at about 1100 cm-1 would be the C-O absorption of the alcohol.
    Alcohol isomers CH3CH2CH2OH CH3CH(OH)CH3 (CH3)2CHOH
    • NMR Shows three peaks:
    delta4.0 multiplet (5 or 6 peaks) integrates as 1.
    delta3.4 broad single, peak integrates as 1.
    delta1.2 sharp, doublet integrates as 6.
    • There are six equivalent protons at delta1.2 suggesting two CH3 groups arranged symmetrically (same chemical
    environment).
    • The chemical shift agrees with CH3-C-OH.
    • Since the absorption is a doublet, there must be -CH- next to each of the two methyl groups. i.e. it must be
    between them.
    • The structure so far would be: CH3-CH-CH3
    • The multiplet at delta4.0 would belong to the -CH- since it integrates as 1 and would be extensively split by the
    two adjacent methyl groups.
    • The delta3.4 absorption would belong to -OH (integrates as 1) which is in the correct range (0.5 - 5.5) for a
    hydroxyl proton. The hydroxyl group would be attached at C2.
    • The final structure is CH3CH(OH)CH3 2-propanol
    • The mass spectrum has the characteristic M - H2O (60 - 18 = 42) peak for an alcohol.
    • The M - CH3 peak (at 45) appears as would be expected for this structure.
    Example No. 2: Mr = 102.1360
    Mr = 102.1360 means that the molecular formula is C5H10O2
    The molecular formula rules out the possibility of an amine.
    IR Strong absorption 1750 cm-1 Hence, carbonyl group of an ester.
    Broad absorption below 1300 cm-1 for the C-O absorption of the ester.

    Ester isomers:
    CH3CH2CH2COOCH3 (CH3)2CHCOOCH3
    CH3CH2COOCH2CH3
    CH3COOCH2CH2CH3 CH3COOCH(CH3)2
    NMR Four absorptions shown:

    3.8 singlet integrates as 3.

    2.2 triplet integrates as 2.

    1.4 sextuplet integrates as 2.

    0.9 triplet integrates as 3.

    There are three protons at 3.8 so it is probably CH 3. The singlet shows that the protons are isolated: could be methyl ester. The chemical shift of 3.8 is in good agreement with
    R-CO-O-CH3 (located at 3.7).
    There are two protons at 2.2 suggesting a CH 2 group.
    The chemical shift agrees with -C-CH2-CO-O-R'.

    The triplet splitting further suggests that there is an additional CH 2 neighbour (see absorption at 1.4).
    The structure so far would be: -CH2-CH2-CO-O-CH3

    The sextuplet at 1.4, integrating as two, would belong to -CH2 - and would
    be split by CH2 and CH3 (see 0.9) groups on either side.
    The chemical shift agrees well with -CH2-C-CO-O-R'.
    The 0.9 absorption would belong to CH3 (integrates as 3). It is split into a
    triplet by a neighbouring CH2.
    The final structure is CH3CH2CH2COOCH3 methyl butyrate

    The mass spectrum shows: 71 M - 31 for removal of OCH3 from


    RCOOCH3
    59 appearance of CO+OCH3 from RCOOCH3

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