Chapter 29: Q60. (page 1196)
Draw the organic products formed in each reaction.


Short Answer


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Chapter 29: Q60. (page 1196)
Draw the organic products formed in each reaction.




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The fibroin proteins found in silk fibers consist of large regions of β-pleated sheets stacked one on top of another. (a) Explain why having a glycine at every other residue allows the β-pleated sheets to stack on top of each other. (b) Why are silk fibers insoluble in water?
Draw the products of each reaction.
(a)
(b)

(c)

(d)
Propose a structure consistent with each set of data.
a. Compound J: molecular ion at 72; IR peak at 1710 \({\bf{c}}{{\bf{m}}^{{\bf{ - 1}}}}\); \({}^{\bf{1}}{\bf{H}}\)-NMR data (ppm) at 1.0 (triplet, 3 H), 2.1 (singlet, 3 H), and 2.4 (quartet, 2 H)
b. Compound K: molecular ion at 88; IR peak at 3600–3200 \({\bf{c}}{{\bf{m}}^{{\bf{ - 1}}}}\); \({}^{\bf{1}}{\bf{H}}\)-NMR data (ppm) at 0.9 (triplet, 3 H), 1.2 (singlet, 6 H), 1.5 (quartet, 2 H), and 1.6 (singlet, 1 H)
Another strategy used to resolve amino acids involves converting the carboxy group to an ester and then using a chiral carboxylic acid to carry out an acid-base reaction at the free amino group. Using a racemic mixture of alanine enantiomers and (R)-mandelic acid as resolving agent, write out the steps showing how a resolution process would occur.
Besides asymmetric hydrogenation (Section 29.4), several other methods are now available for the synthesis of optically active amino acids. How might a reaction like the Strecker synthesis be adapted to the preparation of chiral amino acids?
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