Assigned problems are in purple

For test #2:

Chapter 16 problems:

49,81b,d,106a,c

Chapter 17 problems:

# 46

Extra "Study Questions"

1.         What are alternate names for adrenaline and noradrenaline?

2.         What is the structural difference between the following: amphetamine, epinephrine and albuterol?  What two structural features do all have in common?

3.         Gives uses and/or occurrences of the following:

            a.)        barbiturates, like pentobarbital

            b.)        nicotine

            c.)        cocaine and novocain

            d.)        morphine, codeine and heroin

4.         Which in question 3. are amines and which are amides?

5.         Which in question 3 occur naturally in plants (alkaloids) and which are synthesized?

6.         Give the product of the following reactions:

            a.)

            b.)

 Answers to amine study questions

  1.   another name for adrenaline is epinephrine; for noradrenaline is norepinephrine

  2.   Amphetamine is a mixture of two optical isomers (more on  this on Thursday);  epinephrine contains three additional -OH groups and one less -CH₃ compared to amphetamine; albuterol contains 4 additional carbons compared to adrenaline; all contain a benzene ring and an amino group two carbons away

3,4,5

       a.) sedative and sleep-inducers, amides, synthetic

       b.)   drug found in tobacco; amine; natural alkaloid

       c.) cocaine is a pain-reliever, amine; natural alkaloid

           Novocain is a pain-reliever; amine; synthetic

       d.) morphine is a pain reliever (addictive); amine; natural alkaloid

            codeine is a pain reliever and antitussive (addictive); amine; most is synthesized from morphine

            heroin is a drug of abuse (“pain reliever”) (very addictive); amine; synthetic (made from morphine)

6.

                        a.)

                        b.)

Chapter 18 problems:

9,17,19,33b,c,d,35a,b,c,37,39,43a,53,57,59,67a,b,71,87a,c,89,93,95,97,98a,b,109 (skip chitin),111,122,129,130

ANSWERS: 98a - reducing; 98b - nonreducing

More study questions for CARBOHYDRATES

 Study Questions:

  1. What is the requirement for a mirror-image isomer (enantiomer) and which of the following have these isomers?

2.         What is the difference between D- and L- glucose?

3.         What is “galactosemia”?  How is it treated?

4.         How do people with A, B, or O blood type differ with respect to carbohydrates?

5.         How is high-fructose corn syrup made?

6.         What is dietary “fiber”?

7.         Why is glycerol not a carbohydrate?

8.         What 3 forms does galactose have in solution?

9.         What is the difference between ribose and deoxyribose?

10.       Name 3 hexoses and 3 disaccharides.

Answers to Study Questions:

1.         4 different atoms or groups attached to a carbon. 

            A. and B. only

2.         They are mirror-image isomers (enantiomers):

            mirror images around all 4 chiral carbons.

3.         High galactose levels in the blood which will result in mental retardation.  Restrict galactose  (in milk products) in the diet.

4.         A - have a terminal µ-N-acetylgalactosamine

            B - have a terminal µ-galactose     AB both,  O neither

5.         Corn starch ^enz.® glucose ^enz.® glucose and fructose

6.         Mostly cellulose, if insoluble, and pectin, if soluble.

7.         No aldehyde nor ketone group

8.         µ, b, and “open-chain” or aldehyde

9.         Deoxyribose is missing an oxygen at C#2

10        Glucose, galactose, fructose.

            Maltose, lactose, sucrose

Study Outline for Test #2 (part a) - CHEM 110 summer 2006

Be able to give the products formed when an ester is broken apart using NaOH (a carboxylate and an alcohol are formed)

Know how structure relates to water-solubility and how to increase solubility by creating charge (ionization).

Recognize amine and amide groups.

Know how to classify amines (primary, secondary, tertiary)

Be able to name amines using “common names” (like ethylmethyl amine)

Know about water solubility, especially of amines.

Be able to predict the structure of an amine after it reacts with an acid and the effect this has on its solubility and volatility.

Know the reaction, using heat or DCC, for the formation of amides.

Recognize the structure of “phenethylamine”.

Study Outline for Test #2 (part b) - CHEM 110 summer 2006 

Recognize “chiral carbons”, enantiomers (mirror-image isomers) and their physical, especially rotation of plane-polarized light, and chemical relationships.  Know what “D” and “L”, “dextrorotatory” and “levorotatory”, refer to. (Answer: D and L refer to the differences in the names of mirror-image isomers due to their 3-D structures while dextrorotatory and levorotatory refer to the ability of these isomers to rotate plane-polarized light to the right or to the left.)

Recognize the structure of a carbohydrate. (What is required for something to be a carbohydrate?)

Know and be able to use the following terms: aldose, ketose, tetrose, pentose, hexose. 

Recognize the “ring” (Haworth) structures of: glucose, galactose, fructose, ribose, 2-deoxyribose.

Know what the following mean: blood sugar, dextrose, maltose, lactose, sucrose, (table, cane or beet         sugar), cellulose, starch, amylose, amylopectin, fiber.

Know what “open chain”, alpha- and beta- refer to.

Know what carbons are linked together when looking at a carbohydrate structure.

Know what reacts positively in the Tollens test and what is the evidence for the test.

Know what monosaccharides are responsible for “blood types A, B, AB, and O” and the importance of     these.

Know about galactosemia and lactase deficiency.

Know the relative sweetness of lactose, glucose, sucrose, fructose and aspartame. Know what “high-fructose corn syrup” is and how it is made.

Know material on handout study questions and assigned problems in book.

Assigned problems are in brown

For test #3:

Chapter 19 problems

1,3,9,13,17,19a,b,c,23,27 (palmitic acid is 16:0),35a,b,d,37,43b,49,53,55,59,69,83,87,117b,c

"Study Questions" for lipids

  1.       What properties do all lipids share?

  2.       What are the features of common fatty acids?

  3.       To what physical property does the number of double bonds in a fatty acid relate?

  4.       What are omega-3 fatty acids and what is there relationship to diet?

  5.       How are fats and oils similar and how are they different?

  6.       What makes a substance a steroid?

  7.       What is the use of cholesterol and phosphatidyl choline in the body?

  8.       Where do trans fatty acids come from and what is there affect on health?

  9.       How are the components of the cell membrane arranged?

10.       What two components is “cholesterol ester” made from?

11.       What are the 4 classes of lipoproteins and what is the function of some of them in the body?       How are some of them related to atherosclerosis?

12.       Give an example of “partial hydrogenation of vegetable oil”.

13.  Predict the order of the melting points of triglycerides containing fatty acids, as follows:

            (a) palmitic, palmitic, stearic

            (b) oleic, stearic, palmitic

        (c) oleic, linoleic, oleic

Answers to Lipid Questions

  1.       insoluble in water

  2.       even number of carbons, straight chains, cis-C=C sometimes

  3.       more C=C make it more fluid with a lower melting point

  4.      Omega-3 have a C=C at the third carbon from the end of the fatty acid and many Americans do not consume enough of them for a healthy diet.

  5.       both are triglycerides but fats are solids and oils are liquids at room temperature

  6.       the 4 fused rings with 5 or 6 sides

7.   cholesterol moderates membrane fluidity and is the starting material for biosynthesis    of other steroids; phophatidyl choline is used in cell membranes and in lipoproteins

  8.   Trans fatty acids are made from natural cis fatty acids during the process of hydrogenation. Trans fatty acids seem to increase cholesterol levels and associated risk of heart disease.

  9.   a bilayer of lipid, primarily lecithin (PC), which can diffuse laterally; proteins float in the membrane and are found spanning the membrane or just attached to one surface; carbohydrate chains are found on the exterior surface only.

10.       cholesterol and a fatty acid

11.       HDL - return cholesterol to liver for processing - “protects” against atherosclerosis

            LDL - can bring cholesterol to arteries - increases risk of atherosclerosis

            VLDL - transport triglycerides from liver to fatty tissue

            chylomicrons - transport dietary triglycerides to liver

12.

13. lowest mp is (c); highest is (a)        

Chapter 20 problems:

3,15 (given structures),16 (given structures), 17,18,23d,35,37,38,41,47,57,63,64,66,69,72,75,76,78,79,80,81,83,

90,91,101,102,111,113,116,117,119,120

Answers:

16 - a. nonpolar    b. polar neutral    c. polar neutral    d. polar basic (+ charged)

18 – glycine does not exist as enantiomers (no D or L forms)

38 – N-terminal is the end of the peptide chain near the –NH₂ or ­ NH₃⁺ end, while the C- terminal end is the end of the peptide chain near the –COOH or COO^- end;

64 – they differ in sequence

66 – the N-H and the C=O as in N-H ^... O=C

72 – see page 623

76a – fibrous have the same secondary (for example, wool has only alpha-helix) while globular (like insulin) have a mix of secondary and random shapes

76b – the body contains more fibrous (like collagen!)

78b – structural in skin, bones and teeth

78c – transport oxygen in blood

78d – store oxygen in tissues

90 – the first is a mix of amino acids and the second is a protein with a change 3-D shape

102 - density

Problems Chapter 21:

1,3,25,39,41,45,53,55,57,105

There are no extra study questions for proteins or enzymes.

Study Outline for Test #3 - CHEM 110 – summer 2006

Lipids:

Know the composition and function of the following:

            Features of common fatty acids, [saturated vs. unsaturated fatty acids (effect of C=C and chain length on melting points), trans-fatty acids, structure of oleic acid & stearic acid,] soaps (including hard water effect on), detergents (including hard water effect on), triglycerides, fats, oils, phospholipids like phosphatidyl choline (lecithin), steroids, cholesterol.

Know what partial hydrogenation refers to.

Know the reactants and products of saponification of triglycerides.

Know about cell membranes, including:

            components and their orientation, movement within membranes.

Know about lipoproteins: their composition and function.

Know how soaps, detergents and phospholipid (in lipoproteins)  work similarly.

Proteins:

Know the following terms:

            Zwitterion (knowing which groups are charged), “complete protein” (like meat) & essential amino acids, D vs. L aa (& which is most common), peptide bond (recognize structure, also),

Know the 4 classes of amino acids and examples of each (glycine, alanine, phenylalanine, serine glutamic acid, lysine). Recognize the chemical features of each class.

Know how aa are joined together and what the structure of typical peptides look like. Know what three components are found in aspartame.

Give the four levels of protein structure.

Know the three examples of secondary structure, alpha helix, beta sheet and triple helix, including differences and similarities, including H-bonding. Know the terms “native state” and “denaturation”. Give examples for denaturing proteins and indicate which forces are broken.

Know forces involved in protein structure and know which is the strongest.

Give examples of globular proteins and examples of the three classes of fibrous proteins: alpha helix (keratins), beta sheet, and triple helix.

Enzymes:

Know these terms:

            substrate, active site

Know effect of pH and temperature on enzyme activity

Know these terms:

            - induced fit

            - zymogen (proenzyme), like trypsinogen

Know how sulfa drugs act as competitive inhibitors

Chapter 23 problems:

 5,19,23,33,35,49,51a,b,52,a,b,c,65,81

Answer 52 a - 3    b - 1    c - 2

Chapter 24 problems:

                  Glycolysis – 9,17,18,23,31a,38,43

Answer for 38: see p. 752 (top)

                  Glycogen – 51,61

                  Gluconeogenesis and hormonal control – 71,81,82

                    Answer 82 - lowers blood glucose through processes      given in class

                  General – 96a,b,c

Chapter 25 problems:

        Fat catabolism – 25,37,43a-d,45,49,51,61

        Fat  biosynthesis – 63,74

    105,106

Answer 74: Because they are made from the two carbon acetyl group of Acetyl CoA

Chapter 26 problems:

17,31,35c,41,58,65

Answer 58: carbon dioxide and ammonia

93,94

Study Questions on Metabolism

  1.       Energy released by burning glucose is present in what 2 forms?  List some uses of ATP’s energy. 

  2.       How is energy released from ATP?

  3.       What is the major way (type of phosphorylation) of making ATP?

  4.       Why is O₂ required in the e-transport chain?  How many ATP’s are made from one FADH₂?  from one NADH,H⁺ ?  from one FAD? 

  5.       What is the function of the Krebs cycle?  What compounds don’t get recycled in it?  (Be precise) 

        How many ATP’s can be made from the Krebs cycle using the e-transport chain?  Where in the cell does it occur?

  6.   How many ATP’s are made by glycolysis (ending in pyruvate) in muscle?  in the liver?  Why are they different?  How many ATP’s from one pyruvate to one acetyl CoA?  How many carbons are there in pyruvate?

  7.   How many ATP’s are made in anaerobic glycolysis?  What is its end product?  When will it occur as the predominant pathway?  What does this end product cause in the muscle?  Can it be reused? 

  8.   How may ATP’s are made from 1 glucose, aerobically?  anaerobically?

  9.   What is catabolism?  anabolism?  glycogenolysis?  Where does glycogenolysis occur completely?  How does insulin affect it?  What is glycogenesis?  How does insulin affect it in the liver?  What other thing does insulin affect?

10.   What is gluconeogenesis?

11.    What are sources for gluconeogenesis?

12.   How are fats used for ATP production, including glycerol and fatty acids?  How many ATP’s can be

                                         O

                                         ||

       obtained from CH₃(CH₂)₆COH    a)  from the fatty acid spiral alone (including priming)?       b)  from complete burning to CO₂ ?        c)         Where do you lose ATP?

13.   What are the 3 ketone bodies?  (Recognize their names.)  Give 4 effects produced by elevated levels of ketone bodies.  What is ketosis?  What is acidosis?  How does the body attempt to deal with an onset of acidosis caused by ketone bodies?

14.   How are fatty acids made?  Where does it occur?

15.   What are the uses of amino acids in the body?  Are they stored in the body?

16.   Give 3 examples of proteins and the rates at which they break down.

17.   What reaction does the body use to make amino acids?  What are essential amino acids?  How do we get them?

18.   How are amino acids used for energy?  What product is always formed and why is this product toxic in high amounts?  What reaction cycle does the body use to detoxify it and what is the overall effect of this cycle?

                 Answers for Questions #1 - 18

  1.   Heat and ATP.  Muscle movement, nerve impulses, anabolism 

  2.   Hydrolysis to give ADP and, occasionally, AMP

   3.   Oxidative phosphorylation

 4.   To accept 2 H atoms,         1.5 ATP’s made                        2.5 ATP’s made                        No ATP’s made

  5.   Trap energy present in Acetyl CoA as ATP                        Acetyl only of Acetyl CoA and CO₂

            10 ATPs made in mitochondria 

  6.   5 ATP in skeletal muscle, 7 in heart muscle and liver

            Requires an ATP to transport an NADH, H⁺ into the mitochondria

            2.5 ATP’s made                        3 carbons

   7.   2 ATP’s made,      Lactic Acid,      under low O₂ conditions,                        soreness                       yes, if used soon.

   8.   30 or 32 ATP’s made                     2 ATP’s made

   9.   Breakdown of molecules to make ATP;                  assembling small molecules into large ones using up ATP;

            the breakdown of glycogen to glucose;                liver;                 decreases it;                  biosynthesis of glycogen form          glucose;                        increases it;                   glucose transport into muscle

10.  synthesis of “new” glucoses from non-carbohydrate materials

 11.    lactate and some amino acids

12.   glycerol of fats gives ATP’s through carbohydrate pathway (glycolysis) and fatty acids undergo fatty acid spiral (beta oxidation); 

            a)         10 ATP’s                       b)         50 ATP’s                      c)         the priming step

13.   acetoacetate, beta-hydroxybutyrate, acetone; acetone on breath, electrolyte imbalance, dehydration, and      rapid breathing; high concentration of ketone bodies in blood;       low blood pH;                rapid breathing

14.   fatty acid synthesis;            cytoplasm

15.   make proteins, supply nitrogen atoms for other compounds, for energy;          No

16.   collagen - 3 years, muscle - 3-6 months, serum proteins (antibodies) - 1-2 weeks

17.   transamination;       essential to the diet because the body can’t make them;   eat them

18.   remove the nitrogen atoms and break down the remaining structure to CO₂ and water;

       ammonia is toxic                            urea cycle;        2NH₃ + CO₂  ®   urea + H₂O