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School of Physical & Mathematical Sciences

Division of Chemistry & Biological Chemistry

H3 Organic Synthesis and Mechanism - Tutorial 4


Alkenes and Alkynes

1) Determine the degree of unsaturation for the following molecular formulae:


(a) C7H10 (b) C6H10O (c) C5H6BrCl (d) C4H9NO

2) Draw the products for the following reaction. The carbon backbone of open
chain compounds should be drawn in their "zig-zag" conformation. Indicate
the stereochemistry of the products clearly.

(a) 1. OsO4
Br2
2. NaHSO3, H2O

1. OsO4
(b) Br2
2. NaHSO3, H2O

1. Hg(OAc)2, H2O 1. BH3, THF


(c) 2. H2O2, NaOH
2. NaBH4

MeO

(d)
H2, Lindlar's catalyst
OH
O

3) Suggest a synthetic route to the following compounds. The main carbon


skeleton should be derived from the starting materials given. You may use
any reagents for your synthetic route.
Br Cl
(a) from
OH

(b) from Br
Cl
School of Physical & Mathematical Sciences
Division of Chemistry & Biological Chemistry

Br

(c) from and


Br
Br + enantiomer

OH

(d) from and


Br
OH + enantiomer

4) With the use of curved arrows, show the complete stepwise mechanisms
for the following reactions (more than one step may be necessary):

H2SO4
(a) H2O
OH

H+X-
(b) X- : any anion

O
(c) OH Br2
Br

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