Organisk kemi, 1,5 hp
(delmoment i kursen Textilkemi med miljökemi, 7,5 hp)
Provmoment:
Tentamen 1
Ladokkod:
Tentamen ges för:
TTM011
TI14 och Exchange TEN16
KOD:
Tentamensdatum:
Tid:
2016-02-24
09.00-1300
Hjälpmedel:
(Open book exam)
Compendium in Organic chemistry for the textile engineering
programme, all handouts, own notes, old exams, language
dictionary.
(Any other printed books not used in the course or any
electronic/digital documents are not allowed on the exam.)
Totalt antal poäng på tentamen:
100
För att få respektive betyg krävs:
Underkänd 0-39,5 poäng
Godkänd
40-100 poäng
Allmänna anvisningar:
Lycka till!
Ansvariga lärare:
Telefonnummer:
Kenneth Tingsvik
0708 164178
Exam in Organic Chemistry for TI14 and Exchange TEN16 2016-02-24
Teacher: Kenneth Tingsvik, tel. 0708164178
Question 1 (8p)
1a) Write the electron configuration for the calcium ion, Ca2+ (2p)
1b) Name two other chemical elements or ions, which have the same electron configuration as
the calcium ion above. (3p)
1c) An electron dot diagramme for O2 is shown below. Draw an electron dot diagram for
HCN. (3p)
O
O
Question 2 (12p)
2a) Which is the dominating type of (secondary) bond between polyamide 6 polymers (see the
structure below). (2p)
2b) Which is the dominating type of (secondary) bond between two pentadecane molecules?
(2p)
2c) Complete the reaction below to show the major compound formed. (3p)
CH3
CH 3
C
NH2
HCl
H
Compound A
2d) Give a systematic name of the compound A in question 2c. (2p)
2e) What different kinds of bonds are there in the compound formed in question 2c? (3p)
Question 3 (10p)
3a) The compound 2,4-dimethyl-2,4-hexadiene reacts with a surplus of HBr. Show the
chemical structure of the major product formed. (5p)
3b) Give a systematic name of the product formed in question 3a. (3p)
3c) Will any optical isomer be formed by the reaction? (Motivate your answer.) (2p)
Question 4 (5p)
There are two isomers with the molecular formula C2H6O. Give the chemical structure and the
systematic names of the isomers.
Question 5 (10p)
Show the chemical structure of the following compounds and mark with a star (*) any
existing asymmetric carbon atom(s) in the compounds:
 3-hexanol
 Heptanal
 1-Aminocyclohexanecarboxylic acid (possibly also called
1-amino-1-cyclohexanecarboxylic acid)
 3-metyl-1-hepten,
 bromochloromethane
Question 6 (5p)
Pelargonic acid or nonanoic acid occurs naturally in the pelargon flower. It is used as a
“natural” and biodegrable herbicide. It is a very badly smelling liquid. However its methyl
ester has a much better smell and taste and could be used as synthetic flavouring.
Show the chemical structure of the methyl ester of pelargonic acid.
(5p)
Question 7 (7p)
Complete the reaction and give the structure and the systematic name of the major product
formed.
CH 3
CH 3
CH2
CH 2
CH2
CH
C
OH
NH 2
O
Question 8 (6p)
Show the Newman projection for the most stable conformer of the compound 2,2,3-trichloro3-methylbutane. (Hint: a chloro atom is much bigger than a methyl group.)
Question 9 (7p)
Acetylsalicylic acid (i.e. the medical Aspirin) is the ester formed by acetic acid and
2-hydroxybenzoic acid. Draw the chemical structure of acetylsalicylic acid.
(Remark: Technically Aspirin is produced by the use of water-free acetic acid, so-called
Acetic anhydride, with sulphuric acid as catalyst.)
Question 10 (7p)
Draw the chemical structures and give the systematic names of the products formed by
(alkaline) hydrolysis of the compound below. (Reaction conditions: 2% aqueous NaOH at
boiling temperature.)
Question 11 (8p)
An aldaric acid has the identical structure of the corresponding monomeric carbohydrate
(aldose) except that the aldehyde group at carbon atom no. 1 and the alcohol group at carbon
atom no. 6 have been oxidized to carboxylic groups. In this way D-glucaric acid is formed by
the oxidation of D-glucose.
11a) Show the Fischer projection formula for the aldaric acid formed by oxidation of
D-xylose. (6p)
11b) How many asymmetric carbon atoms contains the aldaric acid formed. (2p)
Question 12 (10p)
A
B
C
12a) The structure of three different cyclooctadienes are shown above. However in order to
give the correct systematic names, the position of the double bonds must be added to the name
cyclooctadiene. Give the systematic names for the three chemicals. (6p)
12b) One of the cyclooctadienes above is significantly more stable than the others. Which
structure represents the most stable compound? Motivate your answer. (4p)
Question 13 (5p)
For dimethylformamide two resonance forms could be drawn. One form is shown below.
Draw the other resonance form. (Hint: Move the free pair of electrons of the nitrogen atom
to form a double bond etc.) (5p)
O
H
C
N
CH 3
CH 3