Organic Chemistry

724 CHAPTER 17 Carbonyl Compounds I

47. A compound with molecular formula gives the following IR spectrum. When it undergoes acid-catalyzed hydrolysis,
    the compound with the following spectrum is formed. Identify the compounds.


48. Aspartame, the sweetener used in the commercial products NutraSweet and Equal is 160 times sweeter than sucrose. What
    products would be obtained if aspartame were hydrolyzed completely in an aqueous solution of HCl?


49. a. Which of the following reactions will not give the carbonyl product shown?

6 .CH 3 COCH 3 +

O

CH 3 CCl

O

CH 3 CNH 2 + Cl−

O

CH 3 CCl

O

3. Cl−

5 .CH 3 COCH 3 +

O

CH 3 CNHCH 3

O

CH 3 CCl + CH 3 NH 2

O

CH 3 COCCH 3

O O

CH 3 CO−

O

2.

CH 3 COH +

O

CH 3 CNHCH 3

O

CH 3 COH + 4. CH 3 NH 2

O

CH 3 COCCH 3

O O

CH 3 CO−

O

1.

+NH 3 CH 2

aspartame

−OCCH

2 CHCNHCHCOCH 3

O O O

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87654 3210

(ppm)

frequency

Offset: 2.0 ppm

2.5 2.6 2.72.82.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 14 15 16

4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600

Wavelength (μm)

Wavenumber (cm−^1 )

% Transmittance

(^1) H NMR
C 5 H 10 O 2