Organisk kemi, 1,5 hp
(delmoment i kursen Textilkemi med miljökemi, 7,5 hp)
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Omtentamen 2
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Tentamen ges för:
TTM011
TI13, TI12 and Exchange TEN15
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Tentamensdatum:
Tid:
2015-02-18
09.00-1300
Hjälpmedel:
(Open book exam)
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Exam in Organic Chemistry for TI13, TI12 and Exchange TEN15,
2015-02-18
Question 1 (5p)
1a) When the elements litium and chlorine react a salt is formed. Write the electron
configuration of the ions in the salt formed.
.
1b) In nature the element alumina, Al, exists as an ion. Write the electron configuration of this
ion.
1c) Below an electron dot diagramme for O2 is shown.
O
O
Draw an electron dot diagramme for formamide.
Question 2 (5p)
2a) Which is the dominating type of bond between two molecules of
1,2-dimethylcyclohexane?
2b) Which is the dominating type of bond between two molecules of lactic acid?
2c) Phosphorous trihydride or Phosphine can bond a proton and form the phosphonium ion, in
the same way as ammonia can bond a proton a form the ammonium ion (see the reaction
below).
Which different kinds of bonds are there between the atoms in the phosphonium ion?
H
H
P
H
H
H
H
P
H
H
Question 3 (7,5p)
3a) Draw five isomers with the molecular formula
C 3H4Cl2
3b) Give the systematic names of the structures you have drawn in the question above.
Question 4 (5p)
4a) Complete the reaction below to show the major product formed.
4b) Give a systematic name for reactant A and the product formed.
Reaction:
CH 3
CH2
CH 2
CH2
C
CH 3
HC
CH 2
HBr
CH 3
Reactant A
Question 5 (5p)
Show the Newman projection of the most stable conformer of the compound
2,3-dichlorobutane.
(Hint: The chloro atoms are much bigger than the methyl groups.)
Question 6 (12p)
Give the systematic names for the compounds in Appendix 1.
Question 7 (5p)
”Oil of wintergreen” is a heating liniment used for treatment of muscular pain. Its chemical
structure is shown below.
7a) Draw a reaction formula for the synthesis of the liniment.
7b) Give a systematic name for the liniment.
Oil of Wintergreen
?
Question 8 (5p)
Which one of the compounds A and B is the most basic? (Motivate your answer.)
NH 2
CH 3
CH 2
NH
A.
B.
Question 9 (5p)
Bipuvacaine is a drug used by dentists for anaesthetic (“reduction of pain”) before drilling the
teeth. The chemical structure of Bipuvacaine is shown below.
Show the chemical structures of the products formed by alkaline hydrolysis of Bipuvacaine.
(i.e. the reaction between Bipuvacaine and 2% aqueous NaOH at boiling temperature).
CH 3
CH 2
CH 2
CH 2
CH3
H
N
N
C
O
CH3
Bupivacaine
Question 10 (7,5p)
Show the resonance forms of 1,3-pentadiene.
Question 11 (5p)
By oxidation of the aldehyde group of a monsaccharide (also called an aldose) to a carboxylic
group a so-called aldonic acid is formed. Thus D-glucose could be oxidized to D-gluconic
acid.
The aldonic acids are important high-value chemicals which are used for many applications.
E.g. D-xylonic acid (formed by oxidation of D-xylose) is used for the synthesis of many
important chemicals and as additives in pharmaceuticals, food and agriculture products.
Applications are even found in cement, where D-xylonic acid acts as a cement retardant for
control of the setting time.
11a) Draw a Fischer projection formula for D-xylonic acid.
11b) Mark the asymmetric carbon atoms in D-xylonic acid with an asterisk (*).
Appendix 1
CH3
CH2
6a)
6b)
CH3
CH3
CH 2
CH 2
C
CH
CH2
CH 3
CH 2
C
O
6c)
HO
C
CH 2
CH
CH 2
CH
C
CH3
CH 3
NH 2
CH 2
CH2
CH 2
CH3
6d)
O
C
6e)
CH3
O
H
CH 2
CH 2
CH3
OH
6f)
6g)
CH3
CH
CH2
CH 2
CH2
CH 2
OH
O
6h)
CH 3
C
CH2
CH 2
C
CH3
OH
CH
CH
CH2
CH 3
CH3
CH 3