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ORGANIC
CHEMISTRY II
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SPRING 2004
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Week
of: |
Mon. |
Weds. |
Fri. |
Lab |
Report |
Due |
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March
22
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17
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17
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17
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#28.1
Characterization
Project 5.2: Grignard reaction: preparation |
Abstract,
results
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in
lab week of April 5
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Exam II: Tues. March 23
Chapters 11, 12, 13
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March
29
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18
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18
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18
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Project 5.2: Grignard reaction, part 1 |
Abstract,
results, conclusions
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in
lab week of April 19
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April
5
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19
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19
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no
class
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Project 5.2, part 2 |
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April
12
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no
class
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19
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20
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Project
5.2, characterization
Project
12.1: Thiamine-Catalyzed Benzoin Condensation - set up reaction |
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April
19
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20
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21
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21
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Project 12.1 continued |
Abstract,
results
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in
lab week of April 26
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Exam III: Tues. April 20
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April
26
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21
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22
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22
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#27
Enolate Chemistry
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yellow
pages
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end
of lab
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May
3
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23
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23
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no
class
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Clean
up and check out
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805
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Ch. 17: Nucleophilic Addition Reactions of Aldehydes
and Ketones
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808
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The carbonyl group adds water or hydrogen halides
to form a geminal diol or halohydrins, respectively
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810
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The carbonyl group adds an alcohol forming a hemiacetal
and an acetal
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817
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Acetals and thioacetals are used as protecting groups
for the carbonyl group of aldehydes and ketones
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821
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Carbohydrates are polyhydroxyaldehydes and ketones
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827
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Hemiacetal isomers of carbohydrates can equilibrate
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829
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Acetal derivatives of carbohydrates can be prepared
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831
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Oligosaccharides are acetal derivatives formed by
coupling two or more carbohydrate derivatives
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832
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A polysaccharide is hydrolyzed under acidic conditions
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838
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Organometallic compounds add to aldehydes and ketones
to produce alcohols
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840
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Boron and aluminum hydrides provide a convenient
source of hydride ion, which adds to the carbonyl group to generate an
alcohol
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846
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Hydride ion in biological systems is provided by
NADH or NADPH
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848
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In the laboratory NADH and enzymes can be used to
reduce ketones enantioselectively
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849
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Aldehydes and ketones can be completely reduced
using amalgamated zinc and acid
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852
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An aldehyde is readily oxidized to a carboxylic
acid
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853
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Carbohydrates are oxidized to mono- and dicarboxylic
acids, depending on the reagent used
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856
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Summary
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869
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Ch. 18: Addition-Elimination Reactions of Aldehydes
and Ketones
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870
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A primary amine reacts with an aldehyde or ketone
to produce an imine, also called a Schiff base
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872
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Hydrazines and hydroxylamine convert carbonyl compounds
to stable derivatives
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874
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Imines, hydrazones, and oximes can be hydrolyzed
to regenerate the corresponding carbonyl compound
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876
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The Wolff-Kishner reaction combines hydrazine and
base to convert a carbonyl to a methylene group
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878
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An imine is reduced by hydride ion to form an amine
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879
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Imines play an important role in structural biology,
forming crosslinks that can stabilize proteins
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881
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An imine bond is important for transforming light
energy into molecular motion and electrical impulses
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884
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Coenzymes are sometimes positioned within an enzyme
active site by an imine linkage
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889
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Imine bond formation and hydrolysis play a significant
role in amino acid metabolism
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898
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Phosphorous ylides are prepared from phosphonium
salts
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899
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The Wittig reaction combines a phosphorous ylide
with an aldehyde or ketone to produce an alkene
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901
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The Wittig reaction is not stereospecific
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902
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Alkoxy-substituted phosphorous ylides are used to
prepare homologous aldehydes
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903
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Phosphonate ylides convert aldehydes and ketones
to alkenes, too
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907
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Summary
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917
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Ch. 19: Addition-Elimination Reactions of Carboxylic Acids and derivatives |
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918
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Reactions of Carboxylic acids are dominated by the
presence of the proton
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921
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An ester can be made directly from a carboxylic
acid under acidic conditions
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924
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A lactone is formed from a hydroxy acid under mildly
acidic conditions
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926
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Formation of a tetrahedral intermediate dominates
the reaction mechanisms of carboxylic acid derivatives
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928
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The reactivity of carboxylic acid derivatives varies
according to the nature of the carbonyl substituent
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929
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An acid chloride is readily prepared from a carboxylic
acid
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931
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Acid chlorides react with alcohols to form esters
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932
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In biological systems esters are made from thioesters
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934
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Anhydrides are reactive intermediates that can sometimes
be formed by dehydrating carboxylic acids
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936
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An amide is readily prepared from an acid chloride
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939
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Hydrolysis of carboxylic acid derivatives occurs
via an anionic tetrahedral intermediate under basic conditions
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941
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Hydrolysis of carboxylic acid derivatives occurs
under acidic conditions via protonation of the carbonyl group
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943
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A tetrahedral intermediate is stabilized during
the enzyme-catalyzed hydrolysis of proteins
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948
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Transesterification is the same process as hydrolysis
except that the nucleophile is an alcohol rather than water
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949
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Polyesters are made by condensation rather than
addition
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953
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A nitrile is a carboxylic acid derivative that lacks
a carbonyl group
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955
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Carboxylic acid derivatives can react with organometallic
reagents to form ketones
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959
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Carboxylic acid derivatives react with organometallic
reagents to form alcohols
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960
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Hydride ion reduces a carboxylic acid and some of
its derivatives to the corresponding alcohol
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962
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Some carboxylic acid derivatives can be reduced
to aldehydes
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963
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Amides and nitriles can be reduced to amines
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965
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Summary
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