Chem 109 C Fall 2015 Armen Zakarian Office: Chemistry Bldn 2217

Transcription

1 Chem 109 C Fall 2015 Armen Zakarian ffice: Chemistry Bldn

2 syllabus! ffice ours Mon, Wed - 9:00-9:50 am (or )! Chemistry building, room 2217! website: - zakarian@chem.ucsb.edu make sure to include Subject: 109C

3 grading! 500 points total! three midterm exams: 100 points each lowest scoring is dropped! a 300 point final exam " A % " B % " C % " D % Disclaimer: no make ups for any tests

4 holidays - no class! Thanksgiving Wednesday, 11/26! Veteran s day Wednesday, 11/11! Stay tuned for other possible news regarding no class

5 exams! all exams will be in this room, BRDA 1610! All hats, cell phones, PDAs, calculators, ipods, and other electronic devices must remain stowed away during exams! Bring a picture ID to the exam! No makeups a missed test can be the dropped test

6 course outline Part 7! Chapter 21 Carbohydrates! Chapter 22 Amino Acids, Peptides, and Proteins! Chapter 23 Catalysis and Enzymes! Chapter 24 The rganic Mechanisms of the Coenzymes! Chapter 25a rganic Chemistry of Metabolic Pathways! Chapter 25b Terpenes! Chapter 26 Nucleosides, Nucleotides, and Nucleic Acids [Part 8 Chapter 29 - Synthetic Polymers etc.]

7 formula for success: read the textbook before coming to class come to class do the suggested problems do the suggested problems again study with a friend or in a group put emphasis on understanding vs. simple memorization

8 formula for success:

9 formula for success: I will use a combination of: # blackboard # PowerPoint, mostly for large biomolecules and Practice Proiblems read it do problems

10 Biomolecules carbohydrates, sugars, saccharides >50% of all biomass D-glucose

11 Biomolecules carbohydrates, sugars, saccharides >50% of all biomass lipids fats/oils terpenes steroids, etc. butter D-glucose cholesterol

12 Biomolecules carbohydrates, sugars, saccharides >50% of all biomass lipids fats/oils terpenes steroids, etc. amino acids, peptides, proteins butter D-glucose cholesterol - N + 3 L-alanine

13 Biomolecules carbohydrates, sugars, saccharides >50% of all biomass lipids fats/oils terpenes steroids, etc. D-glucose amino acids, peptides, proteins butter cholesterol - N 3 + L-alanine nucleotides, nucleosides, RNA, DNA N N N N purine

14 Synthetic (man-made) Compounds: polymers (plastics): N etc Ph Ph Ph Ph polystyrene etc N N N N N N pharmaceuticals KEVLAR NC 3 N N penicillin S C 2 Cl Zoloft Cl aspirin N morphine

15 Review of Stereochemistry rganic chemistry - chemistry of carbon, C Valence number: 4 C C C

16 Review of Stereochemistry chirality Wikipedia: An object or a system is chiral if it cannot be superposed on its mirror image. A chiral object and its mirror image are called enantiomorphs (Greek opposite forms) or, when referring to molecules, enantiomers. A non-chiral object is called achiral (sometimes also amphichiral) and can be superposed on its mirror image.

17 Review of Stereochemistry chirality Wikipedia: An object or a system is chiral if it cannot be superposed on its mirror image. A chiral object and its mirror image are called enantiomorphs (Greek opposite forms) or, when referring to molecules, enantiomers. A non-chiral object is called achiral (sometimes also amphichiral) and can be superposed on its mirror image.

18 Review of Stereochemistry chirality Wikipedia: An object or a system is chiral if it cannot be superposed on its mirror image. A chiral object and its mirror image are called enantiomorphs (Greek opposite forms) or, when referring to molecules, enantiomers. A non-chiral object is called achiral (sometimes also amphichiral) and can be superposed on its mirror image. chirality in Euhadra snails

19 Review of Stereochemistry

20 Review of Stereochemistry C 2 C C D-glyceraldehyde

21 Review of Stereochemistry C C 2 C C C C 2 D-glyceraldehyde L-glyceraldehyde

22 Review of Stereochemistry C C 2 C C C C 2 D-glyceraldehyde L-glyceraldehyde C C 2 C C C C 2

23 Chem 109 C Fall 2014 Armen Zakarian ffice: Chemistry Bldn 2217 CAPTER 21

24 REMINDER! ALL TESTS WILL BE A MIX F REGULAR AND MULTIPLE- CICE QUESTINS 50 : 50

25 Carbohydrates: Introduction extremely widespread in biosphere, >50% of all biomass! main functions: 1) source of energy 2) cell-cell communication, recognition! origin of name: carbo (C) + hydrates ( 2 ) = C n ( 2 ) n = C n 2n n! main source: photosynthesis in plants photosynthesis reaction:

26 sugars exist in cyclic form Carbohydrates: Introduction

27 based on number of single carbohydrate units monosaccharides (simple carbohydrates) Carbohydrates: Classification

28 based on number of single carbohydrate units monosaccharides (simple carbohydrates) Carbohydrates: Classification disaccharides

29 based on number of single carbohydrate units monosaccharides (simple carbohydrates) Carbohydrates: Classification disaccharides oligosaccharides: 3 to 10 units polysaccharides: >10 units

30 based on carbonyl group Carbohydrates: Classification aldoses have aldehyde group ketoses have ketone group

31 based on # of carbons in chain Carbohydrates: Classification D-glucose D-arabinose D-erythrose

32 Carbohydrates: Classification The D and L notation D-glucose L-glucose

33 Carbohydrates: Classification The D and L notation D-glucose L-glucose D-glyceraldehyde L-glyceraldehyde

34 Carbohydrates: Classification PRBLEM 1 (modified) Classify the following monosaccharides arabinose sedoheptulose mannose

35 Carbohydrates: Configurations of Aldoses

36 Carbohydrates: Configurations of Aldoses Number of stereoisomers = 2 n n is number of stereocenters

37 Carbohydrates: Configurations of Aldoses Number of stereoisomers = 2 n n is number of stereocenters D-glucose

38 Carbohydrates: Configurations of Aldoses Number of stereoisomers = 2 n n is number of stereocenters D-glucose total number of stereoisomers for aldohexoses:

39 Carbohydrates: Configurations of Aldoses Number of stereoisomers = 2 n n is number of stereocenters D-glucose total number of stereoisomers for aldohexoses: total number of stereoisomers for D-aldohexoses:

40 Carbohydrates: Configurations of Aldoses Rebuilding Table 21.1 (p. 982)

41 Carbohydrates: Configurations of Ketoses

42 Carbohydrates: Epimers epimers: diastereomers that differ in configuration at only one asymmetric center

43 PRBLEM 8 (modified) ow many stereoisomers are possible for a. 2-ketohexose Carbohydrates: Epimers b. an aldoheptose c. a ketotriose