CHE 1000 Tutorial Sheet 12 - Organic Chemistry
CHE 1000 Tutorial Sheet 12 - Organic Chemistry
CHE 1000 Tutorial Sheet 12 - Organic Chemistry
QUESTION ONE
(i) H3C CH3 (ii) H3C C CCH3 (iii) H2C C CH2 (iv) H3C C N
O
(v) (vi) H3C O CH3
H CH3
(d) What two hybrid orbitals overlap to form the C-C sigma () bond in acetaldehyde, CH3CHO
(e) What two hybrid orbitals overlap to form the C-C -bond in acetonitrile, shown below:
H3C C N
(f) What two hybrid orbitals overlap to form the C-C -bond in allene, H2C=C=CH2
(g) How many sigma bonds and -bonds are in 1-buten-3-yne?
H2C C C CH
H
(h) How many -bonds and pi-bonds are in propyne?
H3C C CH
1
(i) Calculate the formal charge for the following atoms in the compounds below:
O Br Br
(i) (ii) C N (iii) N N N (iv) Al
N Br Br
H3C O
(j) Arrange the following bonds according to the correct bond length, with the longest first
1. C C 2. C C 3. C C
QUESTION TWO
(a) With reference to hybridisation, how many types of carbons are found in millions of its
compounds? For each type of carbon, state how many other atoms are bonded to it and also
the types of bonds (i.e. single bond/double bond/triple bond), including number of each type
of bond.
(b) Identify the types of bonds present as (spn-s), (spm-spn) , (p-p)- and - bonds, in the
molecules shown below:
O O
O or CH3COCOOH
(i) H C O same as
C C H H
H
H O O
O H
H H O
C C H or N
C same as N
(ii) H C N C H
O
H H
C C H
H H
H H
NH
C C N same as
H C C H
H H
H
2
QUESTION THREE
(a) Draw the molecular orbital diagram (picture) for the following molecules:
H H
H O H (iv)
(iii) C O H C C C H
(i) H C H (ii) H C H
C N H H H H
H H
H
(b) Identify the different types of carbon atoms and also point out which hydrogens are
tertiary, secondary and primary in the molecule given below:
CH3 CH3
H2
H3C C C C CH3
CH3 H
(c) Identify the different types of hydrogens in the following molecules, show how many allylic,
vinylic, acetylinic hydrogens are in each molecule.
H H
H H
H C H H
C C
H H H C C C
H H H C
H H C H
HH H H H
H B
A