Scribd
Upload
255 views

Tutorial 7

1) The document provides information on organic synthesis and mechanisms including spectroscopy, alcohols, ethers, and epoxides. It includes 5 questions related to assigning proton signals, proposing structures based on data, identifying compounds from NMR and IR spectra, proposing synthetic routes, and explaining reaction mechanisms. 2) Question 4 asks to propose synthetic routes for several compounds using available reagents which include bromine, alcohol, bromoalkane, and inorganic reagents. 3) Question 5 briefly explains the formation of an epoxide under basic conditions from an alkyl chloride and the lack of epoxide formation under the same conditions when the starting material is an alkyl bromide.

Uploaded by

Nicholas Ow
Copyright
© Attribution Non-Commercial (BY-NC)
Available Formats
Download as PDF, TXT or read online on Scribd
255 views

Tutorial 7

1) The document provides information on organic synthesis and mechanisms including spectroscopy, alcohols, ethers, and epoxides. It includes 5 questions related to assigning proton signals, proposing structures based on data, identifying compounds from NMR and IR spectra, proposing synthetic routes, and explaining reaction mechanisms. 2) Question 4 asks to propose synthetic routes for several compounds using available reagents which include bromine, alcohol, bromoalkane, and inorganic reagents. 3) Question 5 briefly explains the formation of an epoxide under basic conditions from an alkyl chloride and the lack of epoxide formation under the same conditions when the starting material is an alkyl bromide.

Uploaded by

Nicholas Ow
Copyright
© Attribution Non-Commercial (BY-NC)
Available Formats
Download as PDF, TXT or read online on Scribd
You are on page 1/ 2

School of Physical & Mathematical Sciences

Division of Chemistry & Biological Chemistry

H3 Organic Synthesis and Mechanism - Tutorial 7


Spectroscopy, Alcohols, Ethers and Epoxides

1) With the coupling information given, assign the signals due to Ha, Hb and
Hc .
Hb Ha Jab = 11.8 Hz
Jbc = 0.9 Hz
Hc CN Jac = 18 Hz

2) Propose a structure consistent with each set of data.


a) C9H10O2 , IR absorption at 1718 cm-1

b) C9H12 , IR absorption at 2850-3150 cm-1


School of Physical & Mathematical Sciences
Division of Chemistry & Biological Chemistry

3) A compound with molecular formula C6H10 has a 13C NMR spectrum with 4
lines (δ = 27, 30, 67, 93 ppm). The IR spectrum is shown below. Identify
the compound.

4) The following organic compounds are available in your laboratory:


O
Br OH Br

Using the above compounds (not all of them may be useful), and any other
organic or inorganic reagents, propose a synthetic route each for the
following compounds:
OH
HO HO OH
OH
OH OH

OH

OH

5) Briefly explain the following.

(a) OH
base
O

Cl
OH
base
no epoxide formation
Cl

O
(b)
OH /H+
OH
O

OH

O O

You might also like