Glycine has the molecular formula C2H5O2N. If ten glycines are linked linearly by peptide (condensation) reactions to form an oligomer, what is the correct overall molecular formula?
-
AC20H50O20N10
-
BC20H32O11N10
-
CC20H40O10N10
-
DC20H68O29N10
-
EC20H42O12N10
Answer
Correct Answer: C20H32O11N10
Explanation
Introduction:Forming peptide bonds between amino acids is a condensation process that eliminates water. Accounting correctly for the number of water molecules lost is essential for deriving the empirical formula of a peptide from its monomer building blocks.
Given Data / Assumptions:
- Monomer formula for glycine: C2H5O2N.
- Ten glycines linked linearly create nine peptide bonds.
- Each peptide bond formation eliminates one H2O.
Concept / Approach:The total formula is the sum of monomers minus the water molecules removed during condensation. For n residues in a linear chain, there are n − 1 peptide bonds and thus n − 1 waters lost.
Step-by-Step Solution:
Compute monomer sum: 10 * C2H5O2N = C20H50O20N10.Count peptide bonds: 10 residues → 9 bonds → 9 waters removed.Account for water loss: 9 * H2O = H18O9 removed.Subtract: H50 − 18 = H32; O20 − 9 = O11; C and N unchanged.Resulting formula: C20H32O11N10.Verification / Alternative check:General formula check: for n glycines, overall becomes C(2n) H(5n − 2(n − 1)) O(2n − (n − 1)) N(n) which simplifies to C(2n) H(3n + 2) O(n + 1) N(n). For n = 10, this yields C20H32O11N10, confirming the calculation.
Why Other Options Are Wrong:
- C20H50O20N10: ignores water loss entirely.
- C20H40O10N10 and C20H42O12N10: remove the wrong number of hydrogens and oxygens.
- C20H68O29N10: chemically implausible for a condensation product.
Common Pitfalls:Forgetting that the number of waters lost equals n − 1 for a linear chain, or mistakenly subtracting one water per residue.
Final Answer:C20H32O11N10