Clickers

1
Clickers!
We will work out a synthetic route to achieve the
following overall transformation in four steps.
2
Clickers!
A 1) B2H6, THF 2) NaOH, H2O2 aq. B 1) O3,
CH2Cl2 2) Zn/HOAc C mCPBA, CH2Cl2 D KMnO4,
H3O E Hg(OAc)2, H2SO4 (aq.)
3
Clickers!
KMnO4, H3O
4
Clickers!
KMnO4, H3O
5
Clickers!
KMnO4, H3O
A pTsOH, toluene, D B CrO3, H2SO4
(aq.) C mCPBA, CH2Cl2 D Sn, HOAc
6
Clickers!
KMnO4, H3O
pTsOH, toluene, D
7
Clickers Spectroscopy.
Data on an unknown organic compound whose formula
is C6H8O2 will be presented. The questions will
follow.
8
IR Spectrum
9
Clicker question
The degree of unsaturation in this compound is
A 1 B 2 C 3 D 4
10
Clicker question
The degree of unsaturation in this compound is
A 1 B 2 C 3 D 4
11
Clicker question
From the IR spectrum, what functional group is
likely to be present?
A Ester B Ketone C Carboxylic acid D Nitrile
12
Clicker question
From the IR spectrum, what functional group is
likely to be present?
A Ester B Ketone C Carboxylic acid D Nitrile
13
NMR Spectra.
14
Clicker question
We know the compound contains a COOH group, and
has 3 degrees of unsaturation. Based on this and
the NMR spectra, what other functionality is
present?
A Aromatic ring B Alkyne C Two Alkenes
15
Clicker question
We know the compound contains a COOH group, and
has 3 degrees of unsaturation. Based on this and
the NMR spectra, what other functionality is
present?
A Aromatic ring B Alkyne C Two Alkenes
16
Clicker question
What is the structure of the unknown compound?
17
Clicker question
What is the structure of the unknown compound?