Soal Uts (Kimia Organik) (2011) (1A)

SOAL UTS (KIMIA ORGANIK) (2011)(1A)
Hari, Tanggal : -
Waktu :-
Sifat Ujian :-
Dosen : Dr. Ir. Sukirno, M.Eng
1. Within the last month an experimental drug (now just called PDX 101 – structure
shown in the box below) entered into phase 2 clinical trials for treatment of patients
with advanced multiple myloma or lymphoma (types of cancer). How many carbon
atoms are present in PDX 101? (A) 11 (B) 12 (C) 15 (D) 16 (E) 17
2. How many hydrogen atoms are present in PDX 101? (A) 8 (B) 11 (C) 12 (D) 14
(E) 15
3. What is the relationship of the molecule shown in the box below to PDX 101?
(A) It is identical molecule
(B) It is constitutional isomer
(C) It is conformational isomer
(D) It is configuration isomer
4. How many are electrophiles? (A) 1 (B) 2 (C) 3 (D) 4 (E) All
five
5. How many nucleophiles? (A) 1 (B) 2 (C) 3 (D) 4 (E) All
five
For question 6, 7, and 8 select your question from the following a) selection may beused
more than once, if necessary: (A) configurational isomers (B) constitutional isomers (C)
conformational isomers (D) they are same molecule (just drawn differently)
6. What is the relationship between n-octane and 2,2,3,3-tetramethylbutane?

7. What is the relationship between molecule (1) and molecule (2) shown in the box
below?
8. What is the relationship between molecule (2) and molecule (3) shown in the box
below?
9. Which of the figure (1-5) in the box above represents a gauche form?
(A) 1 dan 2 (B) 3 (C) 4 dan 5 (D) 1,2,dan 3 (E) 3, 4, dan 5
10. Why is the anti-conformation more stabil (lower energy) than the syn- (eclipsed)
conformation?
(A) Eclipsed groups increase the energy of the conformation due to steric repulsion
between the groups on adjacent carbon atoms
(B) Eclipsed conformations have higher energy due to electron repulsion of adjacent
sigma bonds
(C) The anti- conformation is lower in energy due to the opposed bond dipoles
present in this conformation
(D) The anti- conformation is lower in energy because bond lengthns between
tetrahedral carbon atoms in this conformation are shorter
(E) Anti- conformation are not energetically favored over eclipsed conformations
11. How many quartenary carbon atoms are present in the molecule above?
(A) none (B) 1 (C) 2 (D) 3 (E) 4
12. The orientation of the chloro- sunstituent is…..

(A) axial (B) equatorial (C) eclipsed (D) gauche (E) anti
13. How many hydrogen atoms are in equatorial position?

(A) 3 (B) 5 (C) 7 (D) 10 (E) 15
14. Using the three structures shown in the box below, which of these compounds
would be classified as 2° alkyl bromides?
(A) compound 1 (B) compound 2 (C) compound 3 (D) compound 1 and 2
(E)compound 2 and 3
15. Which of the following generic class is likely to be the most nucleophilic?
(A) weak acid (B) ions carrying a positive charge (cations) (C) conjugate bases of
weak acids (D) strong acids (E) H2 and halogen gases
16. The product of the reaction shown is:
The next seven question refer to the diagram below (a plot energy vs degree of bond
reaction about the C2-C3 bond in butane). As appropriate, choose your answer from the
drawings at the top of the next page.
17. Which drawing represents the conformation of the butane at the highest energy
transition state?
18. Which drawing represents the conformation of butane at (3) in the

diagram?
19. Which drawing represents the conformation of butane at the global minimum
energy?
20. Which drawing represents an anti conformation of butane?
21. Which conformation represents a gauche conformation of butane?
22. Which number on the diagram indicates the energy (and the angle of rotation) of a
global minimum? (A) 1 (B) 2 (C) 3 (D) 4
23. Which number on the diagram indicates the energy (and the angle of rotation) of
local minimum? (A) 1 (B) 2 (C) 3 (D) 4
24. Which of the following physical properties will be different for the constitutional
isomers?
(A) Boiling point (B) Solubility in acetone (C) Melting point (D) Vapour pressure at
STP
(E) All of these
25. Which of the following organic compound contain a nucleophilic site?
26. Which of the following is trans-1,3-diclorocyclohexane?
27. In cis-1,3-dichlorocyclohexane yhe cholrine would be:

(A)eq,eq (B) ax,ax (C) one would be ax and one would be eq
28. Tuliskan mekanisme reaksi dari reaksi radikal bebas pada monoklorinasi etana.
Tentukan produk samping dari reaksi tersebut!
29. Tuliskan mekanisme reaksi dari reaksi adisi air dengan katalis asam dari 2-butena!
SOAL UTS (KIMIA ORGANIK) (2011)(1B)
Hari, Tanggal : -
Waktu :-
Sifat Ujian :-
Dosen : Dr. Ir. Sukirno, M.Eng
30. Alkena merupakan suatu senyawa hidrokarbon yang mengandung ikatan rangkap.
Alkena bisa diperoleh dari hasil sintesis ataupun hasil alam.
- Jelaskan 3 sumber alkena dari hasil alam yang Anda ketahui.
- Jelaskan sifat fisika dan kimia alkena.
31. Berikut ini persamaan reaksi eliminasi alkil halida untuk mendapatkan senyawa
alkena.
Jelaskan perbedaan E1, E2, dan ECB.

32. Berikut ini adalah beberapa cara membuat alkena dengan mensintesisnya dari bahan
lain.
Jelaskan perbedaan reaksi 1 dan 2.
33. Senyawa diena terkonjugasi dapat mengalami reaksi adisi 1,2 dan 1,4. Jelaskan
perbedaan antara 2 jenis reaksi adisi tersebut. Jelaskan juga tentang reaksi Diels-Alder.
34. Jelaskan pengertian masing-masing istilah di bawah ini.
29

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SOAL UTS (KIMIA ORGANIK) (2011)(1A)

6. What is the relationship between n-octane and 2,2,3,3-tetramethylbutane?

12. The orientation of the chloro- sunstituent is…..

13. How many hydrogen atoms are in equatorial position?

18. Which drawing represents the conformation of butane at (3) in the

20. Which drawing represents an anti conformation of butane?

21. Which conformation represents a gauche conformation of butane?

27. In cis-1,3-dichlorocyclohexane yhe cholrine would be:

Jelaskan perbedaan E1, E2, dan ECB.

Jelaskan perbedaan reaksi 1 dan 2.

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