1

Learning Objectives and Reading List for

Klein 2nd

edition

Notes
o Review topics are bolded
o This list is subject to minor changes throughout the term check for the latest learning objective list on Connect
Reaction learning objective legend:
(R) Be able to predict the product/use in synthesis
(M) Be able to predict the product/use in synthesis AND draw the mechanism
Learning objectives
Chemical Bonding
Describe chemical bonding in terms of valence bond theory &
hybrid atomic orbitals (sigma and pi bonds)

Sections
1.7, 1.9

Identify and visualize molecular geometry of chemical species using 1.10

VSEPR (the location of nuclei, bonding electrons, and lone pairs of
electrons)

Explain why compounds are polar or nonpolar based on geometry

and bond polarity

Recognize resonance and draw resonance structures of chemical

species

1.5, 1.11

Skillbuilders

Problems

1.7

1.1-1.12, 1.14, 1.19, 1.201.24, 1.34, 1.35, 1.38, 1.41,

1.42 1.46, 1.47, 1.49-1.51,
1.54-1.56, 1.58 1.63-1.67,
2.3

1.8

1.25-1.28, 1.39-1.41, 1.50,

1.55, 1.56, 1.58, 1.59, 1.6869, 1.71-73, 1.74ac, 1.75,
2.43

1.5, 1.9
1.15, 1.29-1.31, 1.36, 1.37,
1.40, 1.43, 1.45, 1.48, 1.57,
1.61, 1.62, 2.10

2.7-2.12

2.6-2.9
2.21-2.38, 2.45, 2.48, 2.51,
2.55, 2.56, 2.59, 2.60, 2.62,
2.66, 2.70-73, 2.75-2.78

Define aromaticity
Determine whether a chemical species is aromatic
Describe the reduced reactivity/increased stability of aromatic
compounds

Last Updated: 5/4/16 11:06 AM

18.1, 18.3
18.5
18.4

18.3
18.15, 18.16, 18.34-18.37,
18.43, 18.68, 18.73

2
Representing organic structures
1.2, 1.3, 2.1-2.2, 2.6
Use a variety of molecular representations (molecular formulae,
Lewis, condensed, bond-line, three dimensional representation with
1.4, 2.4, 2.5
wedges/dashes, orbital overlap like Figure 1.33 on page 23)
o Identify when atoms with a complete or incomplete octet will
2.3
have particular formal charges/lone pairs

Identify functional groups in chemical species as a group of

atoms/bonds that possess a predictable chemical behaviour (alkyl
halide, alkene, alkyne, alcohol, ether, thiol, sulfide, arene, ketone,
aldehyde, imine, carboxylic acid, acyl halide, anhydride, ester,
amide, amine, ketal, hemiketal, acetal, hemiacetal)

Identify and use the terms primary, secondary, and tertiary related
to functional groups (e.g. primary alcohol) and carbocations (e.g.
secondary carbocation)

Name simple alkyl halides, alkenes, alkynes, alcohols, aldehydes,

ketones, esters, carboxylic acids, amides, and thiols (you do not
need to know any common names, just simple IUPAC
nomenclature)

Last Updated: 5/4/16 11:06 AM

1.1-1.3

2.1-2.2, 2.4-2.9, 2.11, 2.39,

2.49, 2.50, 2.52

1.4
1.13, 2.12-2.19, 2.44, 2.53

7.2, 13.1

7.2, 8.3, 10.2, 13.1, 20.2,

21.2, 21.6, 14.11

8.1, 10.1, 13.1,

20.1
Naming Qs: 7.36, 8.1-2,
8.50ab,10.1-4, 10.35-36,
13.1, 13.2ab, 13.30,
13.31adf, 13.32, 20.1-2,
20.44, 20.45abcdei,
21.1bef, 21.2a, 21.3ab,
21.12abdfhi, 21.13bcd

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Stereochemistry
Define the following stereochemical terms:
o Constitutional/structural
isomers
o Conformational
isomers/conformers
o Stereoisomers
o Enantiomers
o Diastereomers

o
o
o
o
o

5.1-5.8

Classify the relationship between pairs of molecules

Draw isomers of a given compound
Determine R and S designation at a chirality centre
Describe the factors that influence alkane and cycloalkane
conformer stability (torsional, steric, and angle strain)
Define the descriptors used to describe conformations of alkanes
and cycloalkanes (chair, boat, eclipsed, staggered)
Classify alkenes as cis/trans and E/Z
Work with different representations of organic compounds
(Fischer, Newman, wedge/dash perspective diagrams, sawhorse)
Describe the biological consequence(s) of stereoisomerism

5.1-11, 21-39, 41-43, 45, 4649, 51-62, 63-64, 65a, 66,

67, 70

5.7

5.68, 5.71

4.7-4.14

5.9
4.8-13

8.4
4.6

8.2
4.7

4.20-38, 46-50, 53-69, 70,

72, 75-76, 79

8.5, 6, 51
4.16, 17, 18, 56

See 5.3, pg 202 and 5.4,

pg 208-209 for examples

Intermolecular forces
o Define and describe hydrogen bonding, London dispersion forces,
1.11,12
and dipole-dipole forces
21.3
Identify the predominant intermolecular forces in a chemical
species or mixture (for compounds that include the important
functional groups in this course: hydrocarbons, alkyl halides,
alcohols, amines, ethers, thiols, sulfides, carbonyls)
Rank boiling/melting points and compare solubility with respect to
intermolecular forces acting in a substance/mixture
Identify the hydrogen bonds between nucleic acids (DNA) and amino 1.12, 24.10
acids in proteins

Last Updated: 5/4/16 11:06 AM

5.1-5.4, 5.8

Meso compound
Stereogenic centre (stereocentre)
Chirality centre
Optical activity
Chiral/achiral

1.10

1.32, 33, 52, 53, 60, 70,

74b, 76-77, 4.78

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Fundamentals of chemical reactions
Describe what equilibrium constants represent (Keq) and what their
relative sizes mean for a particular reaction
Correctly use electron-movement arrow convention (nucleophile to
electrophile) to show how chemical reactions occur
Organic acidity/basicity
Describe what acid constants represent (e.g. Ka, pKa) and what their
relative sizes mean for a particular acid/base reaction (i.e. a
compound with larger Ka is more acidic than one with a lower Ka)
Define strong and weak acids/bases (Arrhenius, Brnsted-Lowry,
Lewis acid/base theories)
Draw conjugate bases and acids of chemical species
Predict chemical behaviour of a conjugate base (or acid) using what
you know about the nature of its acid (or base) (e.g. strong acids
have weak conjugate bases)
Rationalize acidity and basicity by determining relative stability of
ions and molecules using size, electronegativity, hybridization,
induction (electron withdrawal and donation), and resonance
Predict how changes in a reaction mixture shift the equilibrium (Le
Chateliers principle)
Describe how aromaticity impacts acidity/basicity & use this to rank
acids and bases according to strength
Know pKa values for strong mineral acids, hydronium ion, carboxylic
acids, phenols, ammonium/alkylammonium ions, water, primary
alcohols, aldehydes/ketones, esters, terminal alkynes, amines,
alkenes, alkanes
Determine the structure of an amino acid at a particular pH when
given its pKa

Last Updated: 5/4/16 11:06 AM

6.1-6.10

6.2-5

6.6-17, 30, 32-47, 50, 5357(hard), 61ab(hard),

64(hard)

3.1-3.9, 13.2
21.3

3.1-3.12

3.1-3.63, 3.66, 3.69ab,

3.70, 3.71ab, 3.73, 13.413.6, 13.33, 13.34

10.3

10.2

10.5-6, 39, 42

18.5

18.17, 18.41, 18.64

See page 102 for a list of

pKa values (also, see
handout on Connect)

21.39-40

25.2

25.1

25.4-6, 40, 47, 48

5
Introduction to reaction mechanisms
Define, identify, and compare nucleophiles, electrophiles, and
leaving groups
Draw/interpret simple reaction coordinate diagrams (transition
states, intermediates)
Classify reaction types as substitution, elimination, addition,
rearrangement, or proton transfer
Mechanisms of chemical reactions (starts on next page)
Nucleophilic substitution reactions
SN2 (Substrate: alkyl halides; Nucleophiles: hydroxide, alkoxides,
halogen ions, sulfide ions, acetylide ions, enolates of carbonyls
and dicarbonyls, azides and nitriles) (M)
Conversion of alcohols to alkyl halides with SOCl2 or PBr3 (R)
SN1 (Substrates: alkyl halides, alcohols, ethers; Nucleophiles:
water, alcohol, hydrogen sulfide, halogen ions) (M)

Rank carbocations and carbanions in terms of stability

Describe the differences in SN1 and SN2 reactions
(intermediates/transition states, kinetics, catalyst, nucleophile
and substrate)
Identify the nucleophile, electrophile, and leaving group in a
methylation involving S-adenosylmethionine (SAM)

Last Updated: 5/4/16 11:06 AM

6.7
6.6

6.2

6.8-10, 6.26-29, 49, 51-52

7.1-7.9
10.10

7.1-7.8
10.5

7.1-19, 21acegh, 22, 24-27,

29-51, 54abc, 55abd,
59bcde, 56-66, 68-70,7273, 77-78, 80, 82, 10.28-29
13.35ab, 18.76

13.9 (points 1 and 3)

OMIT carbocation
rearrangements (pg 311314)

6.31, 7.50

7.5, page 302

7.12

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1,2-Elimination
E2 (Substrate: alkyl halides) (M)
E1 (Substrates: alcohols, ethers) (M)

Describe differences in E1 and E2 reactions

(intermediates/transition states, kinetics, catalyst, base and
substrate)

Determine whether SN1/SN2/E1/E2 will occur with a particular

starting material and reagents

Electrophilic addition (alkenes)

Hydrohalogenation (M)
Acid-catalyzed hydration (M)
Identify the nucleophile, electrophile, and leaving group in a
terpene biosynthesis
Reduction and oxidation reactions
Catalytic hydrogenation of alkenes and alkynes (R)
Reduction of alkynes with H2/Lindlars catalyst and Na or Li/NH3
(R)
Reduction of aldehydes and ketones with NaBH4 and LiAlH4 (M)
Oxidation of alcohols and aldehydes with H2CrO4 and PCC (R)
Describe how NADH acts as a biological reducing agent

Define reduction and oxidation in an organic chemistry context

Classify reactions as reduction, oxidation, or neither

Last Updated: 5/4/16 11:06 AM

8.5-8 (OMIT pg 361- top

of 363, follow
instructions during class
for Zaitsevs Rule)
8.9-11 (OMIT DBN and
DBU)

8.3-4, 8.6-7
8.8-9
8.10-12

8.7-8.8, 8.9ac, 8.10, 12-15,

18-21, 22abcdf, 23-29, 3132, 34ab, 35abc, 3739abcdefg, 41abce,
42abde, 43abcde, 44-45,
46bcefghijklmn, 47-49,
53-61, 62a, 63, 65-67, 6872, 73, 75, 76ade,
77acefghijkl, 78, 79acdfij,
80, 82, 86-87, 93

9.1, 3, 10

9.1acde, 2a, 3-6, 10-14,

40egh, 41b, 9.51ac, 52,
53a, 58b, 59, 64b, 65b,
62, 63 69, 72, 79, 90
26.27-28

9.7 (OMIT pg 432-435)

10.5

9.5

9.23-24, 25a, 40d, 55, 57c,

61

13.4, 20.9
13.11
13.10
Follow instructions given
during class regarding the
correct method in
assigning oxidation
states.

13.3-4
13.7

8.12-13 (follow
instructions given during
class for deciding
between SN2/SN1/E2/E1)
9.1-4, IGNORE AntiMarkovnikov additions
26.8

10.9a, 10-12, 37a, 38, 4748, 49a, 51, 57cd, 61-62

13.9-11, 12abcd, 22, 23ac,
35ef, 37ab, 46, 48, 63, 65,
69
20.31-32

7
Nucleophilic addition (aldehydes and ketones)
Equilibrium paths of carbonyls in water (keto-enol
tautomerization in acid and base (M)
Addition of water in acid and base (M)
Addition of alcohols, acid-catalyzed (M)
Addition of ammonia and primary amines, acid-catalyzed (M)
Classify chemical species as hemiacetal, acetal, hemiketal, and
ketal, and imine functional groups
Rank the stability of aldehydes/ketones, hemiacetals/hemiketals,
and acetals/ketals
Hydrolysis of hemiacetals, acetals, hemiketals, and ketals, and
imines (M)
Reductive amination (H2, Pd/C + imine) (R)
Explain why an acid catalyst improves the reaction rate of weak
nucleophile addition
Use ketal/acetal protecting groups in synthesis
Aldol condensation, base-catalyzed (M)

Last Updated: 5/4/16 11:06 AM

10.3, 22.1

10.16, 17, 43, 44, 49b, 6364, 67-68, 74

22.1-3

20.6-7

20.2-3, 20.5

2.74, 20.7, 8ac, 9-10, 11a,

12-14, 16-19, 26acd, 27,
56abcefg, 57, 62, 63bcde,
65bc, 67, 70, 72-74,
84abcde, 85-86, 94(hard)
23.16

23.6

23.3

10.7, 20.1
20.4-5

20.5
22.3

22.2-4

22.15-17,19, 25-27, 67-68,

71-73, 76, 84c, 87b

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Carbohydrates
Define carbohydrate
Classify carbohydrates by a variety of features:
o Number of carbons (triose, tetrose, pentose, hexose,
heptose)
o Functional group (aldose, ketose)
o D, L
o Number of sugar units (monosaccharide, disaccharide,
oligosaccharide, polysaccharide)
o Pyranose, furanose
o Disaccharide and polysaccharide linkages using
numbering of linking carbons, alpha/beta relationship in
branched and linear structures
o Reducing, non-reducing
Determine stereochemical relationships between carbohydrates
(enantiomers, diastereomers, epimers, & anomers)
Draw the structure of glucose (this is the only carbohydrate
structure you need to know)
Hemiacetal/hemiketal formation to form pyranoses and furanoses
(M)
Acetal/ketal formation (glycosidic bond formation) (M)
Hydrolysis to hemiacetals/hemiketals and to open chain carbonyl
form (M)
Redox: Tollens reagent (Ag(NH3)2+ in H2O), HNO3, and NaBH4 (R)
Carbohydrates acylation (Ac2O, pyridine) (M) and alkylation (Ag2O,
alkyl halide) (R)
Conversion between ketoses and aldoses (tautomerization) (M)
Recognize when mutarotation is possible and use this concept in
consideration of the structure, reactivity, and optical rotation of
carbohydrates in solution

Last Updated: 5/4/16 11:06 AM

24.15-18, 21, 22, 42-43, 5154, 60, 63, 73-77, 85

24.1-4

24.7-8

24.5

24.4

24.31, 33, 39, 69, 73, 76a

24.27, 45, 49

24.1-3

24.9-12, 46-48, 50, 56

24.5
24.6

24.25, 41c, 70abc, 71

24.40, 41a, 58-59, 67-68,
72

OMIT: Kiliani-Fischer
Synthesis and Wohl
Degradation (bottom pg
1171- middle 1173)

24.23-24, 41d, 57, 61, 70d,

76d

24.14, 15, 26

9
Nucleophilic acyl substitution (carboxylic acids, acid chlorides, acid
anhydrides, esters, amides (M)
Direct conversion of carboxylic acids to acyl chlorides (R),
anhydrides (M), esters (M)
Direct conversion of acyl halides to carboxylic acids (M),
anhydrides (M), esters (M), amides (M)
Direct conversion of anhydrides to carboxylic acids (M), esters
(M), amides (M)
Direct conversion of esters to carboxylic acids (M), amides (M)
Amide hydrolysis (M)
Rationalize the relative reactivity of carboxylic acid derivatives
Reduction of carboxylic acids & esters with LiAlH4 (M)
Claisen condensation (M)

Decarboxylation (M)
Malonic ester/acetoacetic ester synthesis (M)
Amidomalonate synthesis to synthesize amino acids (M)

21.6
21.7

21.1, 2

21.8
21.9
21.10-11

21.14-17, 18aef, 19, 21-23a,

24acde, 25-28, 32abcdfg,
33, 48abcdef, 49,
50abdfghij, 51, 53ace, 56,
60, 61a,b, 62, 64, 65abcd,
66, 67, 68-72, 73bdeg, 75,
81, 82, 86-87, 89, 9293(both hard)

21.12
21.5
22.28-32

25.6
22.4

22.5
25.3

22.5, 6
25.2

22.35-43, 78-79
25.14-16, 57-58, 59c, 60b,
84-86, 89

Integration objectives
Use deuterium (D) in place of hydrogen in chemical reactions to rationalize regiochemistry and stereochemistry (or other
isotopes, such as 18O)
Predict the products and draw mechanisms of intramolecular reactions
Explain experimental results of chemical reactions (e.g. yield, rate, reactions that do not work)
Rank and/or rationalize reaction equilibrium position and/or rate based on the following concepts: acidity, basicity, nucleophilicity,
electrophilicity, sterics, stability, and equilibria
Justify mechanistic steps using proper chemical terminology for both familiar and unfamiliar reactions (e.g. identify the
nucleophile and electrophile in each step)
Provide the product(s) when given the starting material(s) and reagent(s); provide the missing starting material(s) when given
reagent(s) and product(s) in a chemical equation; provide the missing reagent(s) when given the starting material(s) and
product(s)
Solve multi-step synthesis problems using reactions learned in the course (Section 9.3, Skillbuilder 9.10)
Apply chemistry concepts to metabolic processes (e.g. glycolysis, citric acid cycle, etc.) and identify reactions in biosynthetic
routes (e.g. fatty acid biosynthesis). To do this, you do not need to have memorized these pathways!!!
Last Updated: 5/4/16 11:06 AM