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    1. The 1H NMR spectrum of compound C5H10O2 shows signals that indicate it contains a methyl group (d 0.88), another methyl group (d 1.58), and a methylene group (d 3.95). The 13C NMR spectrum shows two carbonyl carbons (d 170.9, 21.7) and the IR spectrum shows an ester carbonyl band at 1735 cm-1. 2. The 1H NMR spectrum of compound C10H12O2 shows signals for an aromatic system with a 1,4-disubstituted benzene ring along with methyl and methylene groups. The 13C NMR spectrum supports the aromatic structure and shows a

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    1. The 1H NMR spectrum of compound C5H10O2 shows signals that indicate it contains a methyl group (d 0.88), another methyl group (d 1.58), and a methylene group (d 3.95). The 13C NMR spectrum shows two carbonyl carbons (d 170.9, 21.7) and the IR spectrum shows an ester carbonyl band at 1735 cm-1. 2. The 1H NMR spectrum of compound C10H12O2 shows signals for an aromatic system with a 1,4-disubstituted benzene ring along with methyl and methylene groups. The 13C NMR spectrum supports the aromatic structure and shows a

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    4 views4 pages

    Questions 1 and 2 Answers1

    Uploaded by

    burhaankhl23
    1. The 1H NMR spectrum of compound C5H10O2 shows signals that indicate it contains a methyl group (d 0.88), another methyl group (d 1.58), and a methylene group (d 3.95). The 13C NMR spectrum shows two carbonyl carbons (d 170.9, 21.7) and the IR spectrum shows an ester carbonyl band at 1735 cm-1. 2. The 1H NMR spectrum of compound C10H12O2 shows signals for an aromatic system with a 1,4-disubstituted benzene ring along with methyl and methylene groups. The 13C NMR spectrum supports the aromatic structure and shows a

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    Question 1 C5H10O2

    H NMR Assignments
    1

    d 1.58, sextet

    O Me d 1.98, singlet
    d 0.88, triplet Me

    d 3.95, triplet
    C Assignments
    13

    d 21.7 d 170.9, disappears in DEPT 135


    inverted in DEPT 135

    O Me d 20.6
    d 10.1 Me
    positive in DEPT 135
    positive in DEPT 135 O

    d 65.8
    inverted in DEPT 135

    IR Spectrum

    Strong band at 1735 cm-1, typical of a non-conjugated ester carbonyl group


    Question 2 C10H12O2
    1
    H NMR Assignments
    The pattern of the signals in the aromatic region (7 – 8 ppm) which appear as a
    pair of doublets are indicative of a 1,4-disubstituted benzene ring. Each doublet
    integrates for two protons.

    d 7.95, doublet

    O
    d 4.35, quartet
    d 2.38, singlet Me
    O
    Me
    d 1.38, triplet
    d 7.22, doublet

    The aromatic signal at d 7.95 is due to the protons ortho to the ester carbonyl
    group. This electron withdrawing group causes deshielding of the signal.
    13
    C NMR Assignments
    It is not necessary to assign all the signals in the aromatic region.

    (*) d 143.2 (0 DEPT 135) ipso

    O
    d 60.5 (- DEPT 135)
    d 21.3 (+ DEPT 135) Me
    O
    Me
    d 10.1 (+ DEPT 135)
    d 127.5
    (0 DEPT 135) (*)
    ipso
    d 166.1 (0 DEPT 135)

    (*) at 128.0 and 129.3 ppm – assignment difficult both give + in DEPT 135.
    The signal at 166 ppm is typical for conjugated ester carbonyl carbons.

    IR Assignment
    Intense band at 1720 cm-1 typical of a conjugated ester carbonyl group.

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