Download Organic Molecules

Name: ___________________
Section: __________
Chem 226 / Dr. Rusay
ORGANIC MOLECULES WORKSHEET (3)
Organic Functional Groups
1.
Using your own words clearly define what are functional groups in organic molecules.
2.
Are the functional groups in the following two molecules the same? Circle one: Yes or No. Circle and name
each function in the structures below
O
a) CH 3 CH 2 CH 2 C OCH 2 CH 3
Name(s):
O
CH 3 CH 2 C CH 2 OCH 2 CH 3
Name(s):
b)
3.
Draw a single correct line structure in the left box of the table below for a molecule that has at least six of the
key common functional groups, where at least one of them has a nitrogen atom present. (Note: The molecule
does not have to actually exist. And, an alkane is not considered as being a functional group.) Circle the
respective functional groups in the structure to correspond with their number and name in the table on the right.
#
Name
1
2
3
4
5
6
4.
Draw condensed structures for molecules with the formula C4H8O that respectively contain:
An alcohol:
An ether:
A ketone:
An aldehyde:
5.
Taxol, isolated from the bark of the Pacific Yew tree, Taxus brevifolia, is an anticancer drug, which was first
studied in the successful treatment of ovarian cancer. In 1969, 1,200 kg of tree bark was processed to produce
10.0 g of pure taxol. The molecule contains 14 functional groups. Circle and number each of the functional
groups in the structure to match the list below it.
#
1
2
3
4
5
6
7
NAME:
Aromatic (Arene)
Aromatic (Arene)
Aromatic (Arene)
Alcohol (2o)
Alcohol (2o)
Alcohol (3o)
Amide
#
8
9
10
11
12
13
14
NAME:
Ester
Ester
Ester
Ester
Ketone
Ether
Alkene
Taxol as a drug is known generically as paclitaxel. It is now widely used in the treatment of many different cancers:
lung, ovarian, breast, head and neck, and advanced forms of Kaposi's sarcoma. A single injectable dose contains 100
mg of the active ingredient, taxol.
Since it would be impractical to harvest enough trees to obtain significant amounts of taxol, a semi-synthetic method
was developed. Needles are harvested from a related, low growing evergreen, Taxus baccata, which is grown in
plantations similar to growing tea. The needles are processed to produce large amounts of a synthetic precursor 10deacetylbaccatin whose structure is shown below.
A major objective of organic chemists is the synthesis of useful compounds such as taxol. Synthetic reactions
mainly deal with “functions” and selectively altering them. The possible reactions available for use in organic
synthesis are vast, almost beyond comprehension, but they are relatively simple when viewed in terms of their
functional group changes and organization.
In the synthesis of taxol from 10-deacetylbaccatin, two alcohol functions in the reactant, 10-deacetylbaccatin, are
converted to the same generic function.
Identify the new generic function by name: _______________________
Four other functions are synthetically introduced. Name them (Two of them are the same.):
Organic reaction stoichiometries are most often in ratios of 1:1, where 1 mole of reactant(s) produces 1 mole of
product(s). Consider 1 mole of 10-deacetylbaccatin reacting to produce 1 mole of taxol. If an oncologist requests
that you to prepare enough taxol to treat 10 cancer patients on a 6 month treatment regimen, which requires 1 dose
per month per patient, how many grams of 10-deacetylbaccatin do you start with in the synthesis of taxol assuming
the reaction yield is 100%?
To begin, provide the molecular formulas and molar masses (MM) for taxol and 10-deacetylbaccatin:
Taxol:
C___ H____ N____ O____
MM _________ g/mol
10-deacetylbaccatin:
C___ H____ N____ O____
MM _________ g/mol
Show your calculation for the amount of 10-deacetylbaccatin that is needed for the synthesis.
10-deacetylbaccatin:
_______ g
Structural features and functional groups within a number of biologically active molecules have been identified as
important factors that relate to their efficacy in treating cancer by way of stabilizing microtubules in cancerous cells
and inhibiting mitosis, which taxol does. (http://en.wikipedia.org/wiki/Taxane) Microtubules are one of the
components of the cytoskeleton, a cellular "scaffolding" that is contained within a cell's cytoplasm, which is made
out of protein. Microtubules have a diameter of ~25 nm and vary in length from 200 nanometers to 25 micrometers.
They are involved in many cellular processes including mitosis, cytokinesis, and vesicular transport.
The highlighted portions in each molecule below plays an important role in the protein interaction which
causes the drug’s effect. (You will have to view this file on-line to see the colors.)
http://chemconnections.org/organic/chem226/Worksheets/%233-Functions-12.pdf
6. Briefly describe how these different compounds and different pharmacophores might all work to stabilize
microtubules relative to protein receptors in the cytoplasm.
Key Common Oxygen & Nitrogen Containing Functions
Alcohol
Ether
HH
| |
H-C-C-O-H
| |
HH
H
H
|
|
H-C- O-C-H
|
|
H
H
CH3CH2OH
CH3OCH3
O
Aldehyde
H3 C CH
CH3CHO
Ketone
O
H3C C
CH3
CH3COCH3
Carboxylic Acid
O
H3C C
OH
CH3COOH
O
Ester
Amide
H3C C
CH3CO2CH3
OCH3
O
CH3
H3 C C
N
CH3CONHCH3
H
Amine
H3 C N CH3
H
CH3NHCH3