Page 28 - FPGEE Medicinal and Organic Chemistry Q&A Book
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Krisman



               hydrogen  bond  in  amides  requires  a  great     Acid derivatives:
                                                                                            O
               amount of energy, and hence amides (aceta-
               mide) would have the highest boiling point
                                                                  (1) Carboxylic acids  R   C    OH
               among the given choices.
                                                                                            O
                            very electron rich
                                                                  (2)  Esters          R    C    OR
                        O
                               ..             O
                   R    C      NH
                                  2      R    C  OH                                         O
                       Amide            Carboxylic acid                                          ..
                                                                  (3) Amides           R    C    NH
                                                                                                    2
               414.  (b)  If  we  carefully  observe  the  given
               choices, we can conclude that they are all car-                               O
               boxylic acid derivatives. In all these compounds,
                                                                  (4) Acid halides      R    C   X
               the hydroxy (-OH) group of carboxylic acid is
               replaced with some other groups.
                                                                                             O
                       When we compared substituted groups,
               we can find only the nitrogen atom of -NH          (5) Anhydride
                                                           2                            R    C   O-CO-R
               (amino) group of amide with unshared pair of
               electrons. This extra pair of unshared electrons                                    -
                                                                      O                           O
               donation stabilizes the carbonyl group of car-               ..
               boxylic acid in amides. Due to this, amides are    R   C     NH                             +
                                                                               2             R    C    NH 2
               the most stable compounds among all acid de-
                                                                     Amide
               rivatives, (Fig: 11.21).                                                      The most stable
                                                                                              acid-derivative
               415. (d) Neutral compounds or compounds with
                                                                               (Fig: 11.21)
               very nill basic characteristics would not be able
               to form salt with diluted H SO .  Among the
                                           2   4
               given choices, only propanamide falls into this   of metabolic wastes such as urea, uric acid,
               category.  Ammonia, ethyl amine and sodium        dissolved salts such as sodium chloride, and
               bicarbonate are mild to moderate bases, and       dissolved organic compounds.  Albumin is a
               form salts with an acid such as diluted H SO .    serum protein that cannot be filtered by the kid-
                                                      2   4
                                                                 neys; and hence is not found in normal adult
               416. (c) Urine is a liquid waste product of the   urine.
               body secreted by the kidneys by a process of
               filtration from blood and excreted through the    417. (c) In organic chemistry, keto-enol tautom-
               urethra. Cellular metabolism generates numer-     erism refers to a chemical equilibrium between
               ous waste compounds, many rich in nitrogen,       a keto form (a ketone) and an enol (an aldehyde
               that require elimination from the bloodstream.    form). The enol and keto forms are said to be
               This waste is eventually expelled from the body   tautomers of each other. The interconversion of
               in a process known as urination, the primary      the two forms involves the movement of a
               method for excreting water-soluble chemicals      proton and the shifting of bonding electrons;
               from the body. Urine is a transparent solution    hence, the isomerism qualifies as tautomerism.
               that can range from colorless to amber but is
               usually a pale yellow. It is an aqueous solution




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