Download Organic Chemistry 4 Problems (2014)

Chemistry 11 (HL)
Unit 7 / IB Topics 10.1 and 20.1
Organic Chemistry 4
Molecules With Oxygen
Use the Organic Chemistry 4 Keynote as your guide and these problems to learn about six
homologous series that contain oxygen.
0.
Can you describe what a functional group is?
A.
ALCOHOLS (Slides 4-10)
1.
Build an alcohol with 3 carbon atoms and 1 hydroxyl group. How many different ways can you
make this molecule?
2.
Draw the structures for these alcohols, using the indicated style. Also indicate the TYPE of
alcohol (primary, secondary or tertiary.
3.
a)
propan-1-ol
(complete structural formula)
b)
2-methylpropan-2-ol
(complete structural formula)
c)
butan-1,3-diol
(condensed structural formula)
d)
2-methylpropan-2-ol
(condensed structural formula)
State the IUPAC name for these alcohols. Also indicate the TYPE of alcohol (primary,
secondary or tertiary.
a)
CH3CH2CH(OH)CH3
b)
c)
d)
CH2(OH)CH2CH2CH(CH3)CH2CH2CH3
O
Chemistry 11 (HL)
Unit 7 / IB Topics 10.1 and 20.1
4.
The boiling point of butane (Mr = 58) is -0.5ºC. The boiling point of propan-1-ol (Mr = 60) is
97.2ºC. Explain the difference in boiling points.
B.
ALDEHYDES and KETONES (Slides 11-16)
5.
Build two molecules with the formula C3H6O. Identify the aldehyde and the ketone.
What term is used for this pair of structures?
Draw the complete AND condensed structural formula for the two molecules. State the
IUPAC name for each one.
6.
7.
Draw the complete AND condensed structural formulas for the following:
a)
ethanal
b)
3-methylpentanal
b)
butanone
State the IUPAC name for the following:
a)
c)
e)
b)
CH3CH2CH2CHO
CH3COCH3
d) CH3CH(CH3)(CH2)3CHO
f)
(CH3)3CCHO (tricky!)
Chemistry 11 (HL)
Unit 7 / IB Topics 10.1 and 20.1
8.
Explain why propanal is more volatile than propanol.
C.
CARBOXYLIC ACIDS (Slides 17 - 19)
9.
Build propanoic acid.
Draw its structure.
Identify the hybridization of each carbon and oxygen atom. Show all the bond angles.
10.
Draw the complete and condensed structural formulas for the following:
a)
11.
ethanoic acid
b)
3-ethylpentanoic acid
b)
CH3(CH2)3CH(CH3)COOH
State the IUPAC name for the following:
a)
c)
12.
Ethanoic acid (commonly known as vinegar) dissolves readily in water, but octanoic acid
(found in goat milk) does not. Suggest a reason for this.
Chemistry 11 (HL)
Unit 7 / IB Topics 10.1 and 20.1
D.
ESTERS and ETHERS (Slides 20 to 24)
13.
Build 2 different esters with 3 carbon atoms. Draw the complete AND condensed structure of
each one and name them.
14.
Draw the complete and condensed formulas for the following:
a)
15.
methymethanoate
b)
butylethanoate
State the IUPAC name for the following:
a)
b)
CH3CH2CH2COOCH2CH2CH3
16.
What is the difference in the structure of an ester and an ether? Show using structures of
containing 2 carbon atoms.
17.
The compound C3H6O2 has two structural isomers. Isomer “A” has a lower boiling point than
isomer “B”. Draw each isomer, and explain the difference in boiling point.
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18.
Rank these molecules in order of increasing boiling point and explain your reasoning.
CH3COCH3
C4H10
CH3COOH
C3H7OH
CH3CH(CH3)CH3