CHEMISTRY 53
ORGANIC CHEMISTRY LABORATORY
EIGHTH LABORATORY, OCTOBER 28, 30, 31, and NOVEMBER 5, 2013
Alkenes from Alcohols: Dehydration of 2-Methyl-2-butanol
1. Before coming to the laboratory:
(1) Read in Williamson, Sixth Edition, Chapter 10, pages 205
CHEMISTRY 53
ORGANIC CHEMISTRY LABORATORY
FIRST LABORATORY, SEPTEMBER 9, 10, 11, 12, 2013
Melting Points and Molecular Models
Before coming to the first laboratory session:
Please read Williamson & Masters, Macroscale and Microscale Organic Experiments, 6
Rebecca (Yi-Shuan) Wang
Lab Partner: Maria Choi
Date Performed: 9/18/13
Chem 53 Section K
Recrystallization of an Unknown
Purpose:
The purpose of this lab was to learn how to identify appropriate solvents for
recrystallization in order to recrystallize ph
Chemistry 53
September 27, 2007 PRINT NAME_Answer Key_
Quiz #1
Print Name of Lab Teaching Assistant _
1.
Draw bond-line formulas of all molecules with no multiple bonds having the molecular formula below:
If stereoisomers are possible, draw each stereoiso
Rebecca (Yi-Shuan) Wang
Lab Partner: Maria Choi
Date Performed: 9/25/13
Chem 53 Section K
Extraction of a Carboxylic Acid, Phenol, and a Neutral Substance
Purpose:
The purpose of this lab was to separate, extract, and purify a carboxylic acid, a phenol,
a
Rebecca Wang
Lab Partner: Maria Choi
Date Performed: 10/23/13
Chem 53 Section K
Nucleophilic Substitution Reactions of Alkyl Halides
Purpose:
The purpose of this experiment was to learn about SN2 and SN1 reactions by observing the
rate of reaction between
Rebecca Wang
Lab Partner: Maria Choi
Date Performed: 10/30/13
Chem 53 Section K
Dehydration of 2-Methyl-2-Butanol to form Alkenes
Purpose:
The purpose of this lab was to synthesize 2-methyl-2-butene and 2-methyl-1-butene from
2-methyl-2-butanol using acid
Rebecca Wang
Lab Partner: Maria Choi
Date Performed: 10/09/13
Chem 53 Section K
Separation of Ferrocene and Acetylferrocene by Column Chromatography
Purpose:
The purpose of this lab was to use column chromatography to separate ferrocene and
acetylferrocen
Rebecca Wang
Lab Partner: Maria Choi
Date Performed: 11/13/13
Chem 53 Section K
Aldehydes and Ketones
Purpose:
The purpose of this lab was to determine the composition of an unknown carbonyl. This
was done by first performing a series of tests, Tollens te
Alcohols from Carbonyl
Compounds
Organolithium (RLi) and
Organomagnesium (RMgX) Reagents
(GRIGNARD REAGENTS)
ADDITION OF HYDROGEN
TO THE -BOND
Choose the appropriate reagents
Choose the appropriate reagents
(1) LiAlH4
(2) H3O+
Choose the appropriate reage
Typical NMR hydrogen-hydrogen coupling constants (J) for pairs of
diastereotopic or heterotopic hydrogen atoms separated from one
another by one or two carbon atoms.
two hydrogens on sp2 carbons
two hydrogens on sp3 carbons
J = 8 Hz
two diastereotopic hyd
Good leaving groups have conjugate acids with low pKa values
Stable Alkoxide Anions have no good leaving groups
_
_
O
_
O
H
H
_
O
O
H
Unstable Alkoxide Anions have good leaving groups
_
_
_
O
O
H
HO
HO
Unreasonable
Leaving Conjugate
Group
Acid
H 3C
0.5
H3
Regiospecific and Stereospecific Reactions of Three-Membered-Ring Cations:
Bromonium Cations, Chloronium Cations and Mercurinium Cations, continued
H
O
H
O
+
O
+
+
H
+
H
+
O
H
+
O
O
H
H
H
Br
Cl
proton
transfer
Hg
+
+H
O
O
proton
transfer
proton
transfer
H
Regiospecific and Stereospecific Reactions of Three-Membered-Ring Cations:
Bromonium Cations, Chloronium Cations and Mercurinium Cations
1-Methylcyclopentene
H
Hg O
Br-Br
CF3
Cl-Cl
Br +
O
Cl +
H
O
H
CF3
+
Hg
+ m.i.
+ m.i.
O
2
H
+ m.i.
O
O
H
+
+
H
+
O
+ m.
Typical NMR hydrogen-hydrogen coupling constants (J) for pairs of
diastereotopic or heterotopic hydrogen atoms separated from one
another by one or two carbon atoms.
two hydrogens on sp2 carbons
two hydrogens on sp3 carbons
J = 8 Hz
two diastereotopic hyd
PRINT NAME _
Chemistry 51
THIRD EXAM
December 6, 2002
For each question below, carefully follow the instructions. Check what you write immediately after
writing it. A pKa Table is attached.
32% 1. First write a retrosynthetic analysis and then write a syn
2009 EXAM #2, Answer to Question 4.
Step 1: proton transfer, consumming the hydronium cation (the catalyst)
+
+
H
H
H
H
+
H
H
O+
+
H
H
H
+
H
H
H
+
O
+
H
O
H
H
H
H
H
Step 2: 1,2-shift of a methyl group
H
H
H
+
H
H
H
H
H
+
+
H
+
H
H
H
H
H
+
+
H
H
H
H
Step 3
PRINT NAME _
STUDENT NUMBER_
Chemistry 51
FINAL EXAMINATION
December 21, 1999
PLEASE PRINT YOUR NAME AND STUDENT NUMBER ABOVE NOW
For each question below, carefully follow the instructions. Check what you write
immediately after writing it. Periodic Table
Chemistry 51
FIRST EXAM
September 28, 2007
1. Draw a bond-line formula that shows stereochemistry clearly (by drawing one dotted
bond from each chirality center to the lowest priority atom or group placed so that it is
pointing away from the viewer) for e
STUDENT NUMBER_PRINT NAME _
Chemistry 51
FINAL EXAMINATION
December 13, 2007
PLEASE PRINT YOUR NAME AND STUDENT NUMBER ABOVE NOW
For each question below, carefully follow the instructions. Think before you write, then
check what you write immediately afte
Organic Chem Review Problem Set
Note: There will be a review Session put on by me (Zach) Tuesday December 13 @ 7:00 in Pearson 104.
Please spread the word so everyone knows!
1. First write a retrosynthetic analysis and then write a synthesis for of each o
Exam #2, 2007, 1 (c)
Retrosynthetic Analysis
Br
8 = 6+2
D
8 carbons
alkyne
C
_
D
R
R
Br
4+2 = 6
_
C
R
OH
Synthesis
Br
S N2
D
HBr, ROOR
_
D
H2, Ni2B
Br
_
S N2
PBr3
OH
51e2 ans 1c 07.cdx
PRINT NAME _
FIRST EXAM
October 2, 2009
Chemistry 51
1. Draw a bond-line formula that shows stereochemistry clearly (by drawing one dotted
bond from each chirality center to the lowest priority atom or group placed so that it is
pointing away from the vie
PRINT NAME _
Chemistry 51
SECOND EXAM
November 6, 2009
For each question below, carefully follow the instructions. Check what you write immediately after
writing it. A pKa Table and a Relative Nucleophilicity Table are printed on the last page.
1. First w
PRINT NAME _
Chemistry 51
SECOND EXAM
November 6, 2007
For each question below, carefully follow the instructions. Check what you write immediately
after writing it. A pKa Table and a Relative Nucleophilicity Table are printed on the last page.
1. First w
PRINT NAME _
Chemistry 51
SECOND EXAM
November 1, 2002
For each question below, carefully follow the instructions. Check what you write immediately
after writing it. A pKa Table is attached.
1. First write a retrosynthetic analysis and then write a synthe
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