Final Exam Review Sheet
Review Session TBA
Chemistry 110b
The final exam questions will seek an integrated understanding of the material found in chapters 14-25.
You will be allowed to use the following when working your final exam: a calculator, molecular models,
15 pieces of unlined white 8.5 x 11 inch paper on which you may hand-write any information to your
liking on both sides of the paper. These “study aids” will be due at the end of the exam period and the
quality of your notes will factor into your final exam grade. Retain a copy of your notes for your own
records. Please consult your prior exam review sheets in preparation for the final exam.
Chapter 22:
1.
Classification of carbohydrates (22.2A, 22.2B), D and L designation- historical aspects and use of
glyceraldehyde as a reference compound, Bijvoet’s contribution to this use of stereochemical
descriptors. Review the R/S system and be able to correlate this system with the D/L system for
glyceraldehyde and the optically active tartaric acids. 9E: 1021-1025, 10E: 1001-1005.
2.
Structural formulas for monosaccharides: be able to translate a Fischer projection into a pyranose,
furanose, or lactone, depending upon the C.1 oxidation state. Be able to do this translation in the
opposite direction as well. Def of  and  pyranose/furanose and pyranoside/furanoside. Use Dglucose as your practice molecule in these transformations-- every organic chemist should know
the structure of this sugar. 9E: 1025-1028, 10E: 1005-1009.
3.
Mutarotation (def.) for hemiacetals and hemiketals--mechanism of this process. 9E: 1028-1029,
10E: 1009-1010.
4.
Glycoside formation- know the mechanism of this process. Definition of aglycone. 9E: 10291031, 10E: 1010-1013.
5.
Origin of the stereoelectronic effects (the anomeric effect) used to explain axial preference of
glycosides, and the enhanced axial preference seen in six-membered hemiacetals (e.g., glucose).
Relevance of substituted cyclohexanes (OH, OMe) in these discussions. Class handout.
6.
Reactions of monosaccharides: methylation, benzylation, esterification, cyclic acetals and ketals
(rules for formation-- 1,3 diols can also undergo this reaction); nature of Tollen’s Benedict’s or
Fehling’s solutions: def. of reducing or nonreducing sugars; Bromine water oxidation of aldosesoutcome of reaction and potential lactone formation; nitric acid oxidation of aldoses--outcome of
reaction and potential lactone formation; periodate oxidations- mechanism and outcome (glycerol,
glyceraldehyde, and dihydroxyacetone) of reaction and utility in structure elucidation; reductions
of aldoses and ketoses with NaBH4 or H2/Pt. 9E: 1032-1042, 10E: 1013-1025.
7.
Fischer’s proof of the relative configuration of glucose: no need to memorize the structures
involved, but be familiar with the reactions (mechanisms not required) and general strategy used
to eliminate the possible structures (know how to predict the maximum number of structures for a
given sugar (e.g., 4 carbon, 5 carbon, 6 carbon, 7 carbon). Could you, for example, use the tools
that Fischer had and propose the relative configuration of an aldopentose, given ample exptl. data?
9E: 1044-1048, 10E: 1027-1029.
8.
The structure of sucrose-- every organic chemist should know it. Review the evidence for its
structure. 9E: 1049, 10E: 1029-1030.
9.
The structure of maltose and cellobiose-- these are easy to remember because they are both
glucose- based and differ only at the glycoside linkage. Review the structural evidence for
maltose and check the method used to determine the nature ( ) of the glycosidic linkage in
each. 9E: 1050-1051, 10E: 1030-1032.
10.
Polymerize maltose to starch (amylose) and do the same for cellobiose. Examine the resulting
structures (Fig. 22.14, 22.17) and recognize the dramatic differences in secondary structure-- a
direct consequence of different primary structure. Be able to explain the origins of the exoanomeric ffect and how this stereoelectronic effect contributes to the observed three-dimensional
structure of cellulose and amylose. Explore the structural similarities of chitin and cellulose. 9E:
1053-1061, 10E: 1033-1039.
Chapter 23:
1.
General structure of triacylglycerols; def and general structure of. oils, fats, fatty acids, and waxes.
Reactions and properties. Def and general structure of soaps, micelles, liposomes. 9E: 10741083, 10E: 1051-1060.
2.
Terpenes and terpenoids. Structure of isoprene. Definition of monoterpenes, sesquiterpenes,
diterpenes, and triterpenes. Be able to identify isoprene units in natural products. 9E: 1083-1087,
10E: 1061-1064.
4.
The general structure, systematic nomenclature (ABCD, , angular methyl), and
reactivity of functional groups in steroids. 9E: 1087-1095, 10E: 1064-1073.
Chapter 24:
1.
The basis of the DL nomenclature for amino acids (aa’s). Review this and the R/S convention one
last time. 9E: 1108-1112, 10E: 1085-1089.
2.
Acid/base behavior of amino acids. 9E: 1112-1115, 10E: 1089-1092.
3.
Racemic syntheses of aa’s. Gabriel synthesis starting from -halo esters or diethyl bromomalonate. For the latter, be able to synthesize a DL amino acid and demonstrate a
mechanistic understanding of the reaction sequence. Be able to use a Strecker aa synthesis and
demonstrate a mechanistic understanding of the reaction. 9E: 1115-1119, 10E: 1092-1093.
4.
Be aware of at least two methods for resolving racemic mixtures of aa’s. 9E: 1116-1117, 10E:
1093-1094.
5.
Determining the primary structure of polypeptides and proteins. Edman, Sanger, C-terminal and
complete sequence analysis. Examples that demonstrate the applicability of these methods. 9E:
1119-1129, 10E: 1094-1104.
6.
Peptide synthesis. Utility of the “Z”, “Boc”, and FMOC protecting groups: conditions for
installation and deprotection. Be able to explain, mechanistically, why these groups can be
cleaved without any amide bond cleavage. 9E: 1129-1131, 10E: 1104-1106.
7.
Activation of the carboxyl group for amide bond formation. The dicyclohexylcarbodiimide
(DCC) method. Be able to explain, mechanistically, how a DCC coupling works. 9E: 1131-1133,
805; 10E: 1107-1108, 807.
8.
Automated peptide synthesis. Be able to outline the steps in the synthesis of a small peptide using
the Merrifield solid-phase approach. Be able to describe the chemical nature of the Merrifield and
Wang resisn. Identify the advantages to the Wang solid-phase approach for a linear, repetitive
synthesis. 9E: 1133-1135, 10E: 1108-1110.
Chapter 25:
1.
The chemistry of DNA sequencing. 9E: 1180-1184, 10E: 1155-1157.
2.
Automated oligonucleotide synthesis. Using a block diagram, be able to outline the steps in the
synthesis of a small oligonucleotide. Don’t worry about the detailed structures of the nucleosides- focus on the overall strategy, the functional groups, and the protecting groups. 9E: 1184, 10E:
1157-1159.