HOME WORK

NAMING ORGANIC COMPOUND

1. Draw structures for each of the following alkanes.
a) 1-bromo-1-chloro-2-methylpropane
b) 5-isopropyl-6-tert-butyl-2,2-diiodo-3-methylnonane
c) trans-1,4-dimethylcyclohexane
d) cis-1-ethyl-2-methylcyclopentane
Draw structures for each of the following alkenes.
a) 4-methyl-2-pentene
b) 3-propyl-1-heptene
c) 2,3-dimethyl-2-butene
d) 3-ethylcyclobutane
e) 2-methyl-1,3-butadiene
f) (Z)-3-propyl-2-heptene
g) (E)-1-bromo-2-isopropyl-1,3-butadiene

2. Berilah nama pada alkane dibawah ini

a).

b).

c)

3. Senyawa-senyawa alkene dan siklo alkena mana yang memiliki stereokimia Z, dan
tuliskan namanya secara lengkap.

4. Senyawa pada soal 4a) diatas, tulis namanya secara lengkap (E/Z) nya
5. Berikan nama pada alkena dibawah, lengkap dengan penamaan E/Z nya

6. Naming EZ. Give the name of the following compounds. Be sure to Indicate
stereochemistry where appropriate (e.g. E or Z).

Arrange the following series of substituents in order of increasing E/Z priority

where 1 = lowest and 4 = highest priority.

a)
b)

Today most vanillin is produced from the petrochemical raw material guanacos (1) which is
reacted with glyoxylic acid by electrophilic aromatic substitution. The resulting
vanillylmandelic acid (2) is then converted to 4-Hydroxy-3-methoxyphenylglyoxylic acid (3) by
oxidation and then to vanillin (4) by decarboxylation

a).. Write the IUPAC name of guaiacol (1) and vanilline(4)

STEREO
1.

Gambarkan proyeksi newman pada karbon 3 dan 4, untuk . konformasi anti,

Asam laktat memiliki isomer bayangan cermin atau enansiomer, yaitu R-asam laktat
dan S-asam laktat. Gambarkan

TOPIC : STRUCTURE PHYSICAL /CHEMICAL PROPERTIES RELATIONSHIP

1.

Identifikasi hibridasi semua atom karbon dan oksigen

2.

Berikan dan muatan formal N dan O pada NO2+

3.

For the following give: 1) the Lewis dot structure, 2) the number of starting valence
electrons, 3) the number of bonding + lone pair electrons, 4) the hybridization(s), 5)
the geometry for each central atoms and 6) tell whether it has a dipole moment or
not. HCOO , CO2 C6H6, NO2 , NO3
,,

4.

, ,

The strongest Brnsted acid is the compound that is easiest to give its proton due to
stabilization of its anion. Arrange the following compounds in order of decreasing acidity.
Which is the strongest acid and explain why.

Show valence electron of N and Cl to calculate their the formal charge, in the benzene azonium
chloride.

+
1.

Untuk species kimia berikut : i)CO32- ii) SH2 iii) NH21- iv) NO21+ v) O3
a) (10 poin) Berikan struktur Lewisnya
b) (10 poin) Berikan hibridasi atom yang digaris bawahi
c) (10poin) muatan formal atom yang digaris bawahi
v) Urutkan substituent berikut menurut naiknya prioritas E/Z
(a)

(b)

(c)

Stability (think heat of hydrogenation):

(d)

(a)

(b)

(c)

(d)

What is the hybridization of the oxygen atom in water?

What is the molecular geometry for ammonia (NH 3)?
What is the electron-pair geometry of the central oxygen atom of ozone (O 3)?
Which of the following molecules does not have a net dipole moment?
H2O , NH3, BF3 , BrF5
a)
What is the molecular geometry for ammonia (NH 3)?

TOPIC : STRUCTURE CHEMICAL REACTION

ADDITION
1.
Ramalkan produk yang diperoleh

2.
Give the stepwise mechanism for the following reaction. Use arrows to indicate
the electron flow and show any intermediates

1.

(10poin) Untuk reaksi soal no.4, gambarkan diagram energy yang

menunjukkan posisi reaktan, intermediate dan produk.

2.

(10 poin) Pada reaksi no.4 , berikan mekanisme reaksi jika selain HBr
ditambahkan pula inisiator radikal bebas ROOR .

3.

(10poin) Senyawa alkena pada soal no.4 diatas, akan di polimerisasikan

menggunakan katalis ROOR. Berikan mekanime reaksi polimerisasi tersebut.

AROMATIC
1. 4-phenyldiazenyl aniline is uses as..
This compound can be synthesized via 2 step of reactions. The first step is azolization of aniline
with HNO2 and HCl. Then, the resulting benzene azonium chloride reacts with aniline to
produce 4- phenyldiazenyl aniline to follow electrophilic aromatic substitution.

+
a) How does the amino group in aniline act as para-director in the electrophilic substitution
reaction.
b) The amino group is activator or deactivator, why?
c) Show the mechanism of the substitution( step by step formation of the electrophile
intermediate, ect.)

Cumena dapat dibuat dari benzene dan propylene melalui reaksi substitusi elektrofilik
aromatic berkatalis asam. Tunjukkan mekanisma pembentukan elektrofilnya serta
mekanisme reaksi substitusinya
Pada reaksi asetilasi p-nitroaniline dengan asetat anhidrat, merupakan reaksi substitusi
elektrofilik aromatic. Jelaskan p-nitroanilin mengarahkan ke posisi para.
ELIMINATION SUBSTITUTION REACTION

Tuliskan mekanisme reaksi dehidrasi pembentukan dimetil eter dengan menggunakan

katalis asam
Write structure of transition state, and product and energy diagram of the reaction SN2
of OCH3 with
a). (S)-2-bromo-3-methylbutane
b).trans-1-chloromethyl-4-methylsiklokexane
Propose product of aqueous solvolysis of the following halide
a) cis-1-iodo-3-methylsiklohexane
b) (2R, 4S)-2-iodo-4-methykhexane
1.
2.

a). SN1 reaction of tert-bromo butana with water

b)E1 reaction tert-bromo butane with water
c) SN2 reaction bromo-propane with OHd) E2 reaction 2-bromopropane with OH-

CARBOXYL SUBSTITUTION
Tuliskan mekanisme reaksinya

What is the major product of the following reaction

Which of the following is an intermediate for the basic hydrolysis of methyl ethanoate?

Which of the following is an intermediate formed during the acidic hydrolysis of acetamide?

What is the major product of the following reaction?

Which of the following is an intermediate in the mechanism of the acid catalyzed formation of an
ester?

Transesterification reaction of triglyceride and methanol reactant can produce fatty ester
a) Show the mechanism of the transesterification using NaOH as catalyst ( step by step
formation of the metoxy, intermediate, fatty ester, diglyceride and monoglyceride
b) Show the mechanism of esterification using acid as catalyst for the following reactant( step
by step formation of the protonized acid, intermediate, .etc.)

Polilaktida adalah polimer untuk membuat plastic biodegradable, dapat dibuat dari
reaksi polimerisasi laktida. Anggap katalis yang digunakan adalah asam (H+).
a). (10 poin). Tuliskan mekanisme reaksi pembentukan polilactida tersebut

Laktida dihasilkan reaksi kondensasi asam laktat, tuliskan reaksi tersebut.

1. Aspirin dibuat dengan mereaksikan asam salisilat dan asetat anhidrida berkatalis asam.

a). Nama IUPAC asam salisilat & aspirin

b). Tunjukan mekanisme reaksinya.

Give the stepwise mechanism for the following reaction. Use arrows to indicate

Test Alternatif
1. Name this compound

Topic1 Test
1. Draw structures for each of the following alkanes.
a) 1-bromo-1-chloro-2-methylpropane
b) 5-isopropyl-6-tert-butyl-2,2-diiodo-3-methylnonane
2. Name this compound

a)

b)

c)

3.

Identify hybridization of atom carbon in the molecule of problem 1.a

4.

Free radical reaction

TOPIC2 Test
1.

Naming Alkenes (25 points)

a) Give the name of the following compounds . Be sure to indicate stereochemistry
( E or Z), where appropriate.

b) Arrange the following series of substituent in order of increasing E/Z priority, from
the lowest to the highest priority.

2.

Physical/chemical reactivity (15 points)

a) Arrange the following series of alkenes in order of stability, from the least stable
to the most stable compound (think heat of hydrogenation):

(i)

(ii)

(iii)

(iv)

b). For molecule (i), show 6 atoms those lay on the plane.
3.

Below is a electrophilic addition reaction.

a) Give the stepwise mechanism for the reaction. Use arrows to indicate the
electron flow and show any intermediates . (20 points)
b) Draw energy diagram to show the number of reaction step, the reactant,
intermediates and product position, and whether the reaction is exothermic or
endothermic process (20 points)
4.

For molecule (i) in the problem 2a above , show the complete polymerization
reaction mechanism using ROOR as radical initiator catalyst. (20 points)

TOPIC3 Test a
1. Name this compound
a). Give trivial name of these popular compound

i).

ii)

iii)

iv)

v)

Give the IUPAC name of below compounds

vi).

vii).

2. Structure, physical/chemical properties

a) For molecule (1.vi), indicate (with number 1-6) the 6 atoms those lay on the plane
and identify their hybridization.
b) Benzene is aromatic compound. The reaction of double bond of aromatic benzene
does give di-bromo benzene. Explain why ? Use energy diagram.

3. Mechanism of electrophilic aromatic substitution.

a). Predict the product and draw the complete mechanism of the following reaction

d) For below reaction, explain whether the amino group acts as activator or

deactivator?

e) Explain whether the amino group act as orto, para or meta director, by drawing the

reaction mechanism of the 3 possibilities (step by step formation of the electrophile,

the intermediates, and the products.)

TOPIC3 Test b
1. Name this compound
a). Give trivial name of these popular compound

i).

ii)

iii)

iv)

v)

Give the IUPAC name of below compounds

vi)

vii)

2. Structure, physical/chemical properties

For molecule (1.vi), show 6 atoms those lay on the plane.
Benzene is aromatic compound. What does aromatic mean?

3. Predict the product of the following reaction give the complete mechanism

ORGANIC CHEMISTRY MID TEST a

CHEMICAL ENGINEERING DEPARTMENT FT-UI
Waktu : 90 menit Dosen : Dr.Ir.Sukirno M.Eng
================================================================
1. Physical/chemical reactivity (15 points)
a) Arrange the following series of alkenes in order of stability, from the most stable
to the least stable compound ,

(i)

(ii)

(iii)

(iv)

b). For molecule (iv), show 6 atoms those lay on the plane.
c) Benzene is aromatic compound. The reaction of double bond of aromatic benzene
does not give di-bromo benzene. Explain why ? Use energy diagram.
2. Below is an electrophilic addition reaction.

a) Give the stepwise mechanism for the reaction. Use arrows to indicate the electron
flow and show any intermediates . (20 points)
b) Draw energy diagram to show the number of reaction step, the reactant,
intermediates and product position, and whether the reaction is exothermic or
endothermic process (20 points)
3. For molecule (iv) in the problem 2a above , show the complete polymerization reaction
mechanism using ROOR as radical initiator catalyst. (20 points)
4. Mechanism of electrophilic aromatic substitution.
a). Predict the product and draw the complete mechanism of the following reaction

b). For electrophilic reaction below, whether the amino in the aniline activates or
deactivates the benzene ring? Explain how it work ?

c) Explain whether the amino group act as orto, para or meta director, by drawing the
reaction mechanism of the 3 possibilities (step by step formation of the electrophile,
the intermediates, and the products.)

ORGANIC CHEMISTRY MID TEST b

CHEMICAL ENGINEERING DEPARTMENT FT-UI
Time: 90 menit, Lecturer: Dr.Ir.Sukirno M.Eng
================================================================
1. Physical/chemical reactivity (15 points)
a). Arrange the following series of alkenes in order of stability, from the most stable
to the least stable compound ,

(i)

(ii)

(iii)

(iv)

b). For molecule (iv), identify the 6 atoms those lay on the plane and give the name
with its E/Z designation.
c). For benzene which is an aromatic compound, its reaction with bromide would
prefer to produce bromo benzene, instead of producing di-bromo cyclohex-diene.
Explain why ? Use energy diagram.
2. Below is an electrophilic addition reaction.

a). Give the complete mechanism for the reaction. Show the intermediates and use
arrows to indicate the electron flow. (15 points)
b). Draw energy diagram to show the number of reaction step, the position of reactant,
intermediates and product, and whether the reaction is exothermic or endothermic
process (15 points)
3. For molecule (iv) in the problem 1a above , show the complete polymerization reaction
mechanism, using ROOR as radical initiator catalyst, up to trimers. (15 points)
4. Mechanism of electrophilic aromatic substitution. (40 points)
a). Predict the product and draw the complete mechanism of the following reaction

b). The hydroxyl group in phenol would affect the reaction rate of the electrophilic
substitution reaction. Explain how it works? It is activator or deactivator.

c). For above reaction, explain how the hydroxyl group in the phenol directs the
electrophilic substitution, by drawing the reaction mechanism of the 3 possibilities
(orto, para or meta), including the formation of the electrophile, the intermediates,
and the products.

TEST TOPIC 4 &5

1. Dalam reaksi substitusi nukleofilik, bandingkan pasangan nukleofil pada soal dibawah
ini, manakah yang nukleofilitasnya lebih tinggi. Berikan alasannya.
a). (CH3)2N- atau (CH3)2NH
b). (CH3)3B atau (CH3)3N
c). H2O atau H2S
2. Dalam reaksi substitusi nukleofilik, pasangan senyawa organo halogen dibawah ini,
manakah yang lebih reaktif terhadap nukleofil OHa) CH3Br atau CH3I
b). CH3CH2I dalam etanol atau CH3CH2I dalam dimethylsulfoksida
c). H2C=CHBr atau H2C=CHCH2Br
3.Berikan penjelasan kenapa mengikuti SN2,SN1, E2, E1 . Tuliskan reaktan, transisi,
produk secara lengkap dengan gambar stereo (R/S orientation) dan gerakan elektron
serta gambar diagram energinya.
a). Reaksi SN2 dari (S)-2-iodoheksana dan CH3CH2S dlm pelarut dimethylsulfoksida.
b).Reaksi SN1 (1-bromo-1-metilpropil) benzene dengan H2O.
c).Reaksi E2 CH3)2CHCHBrCH2CH3 dengan potassium hidroksida
d).Reaksi E1 (1R,2R)-1,2-dibromo-1,2-difeniletana dengan KOH

TEST TOPIC 4 &5

1. Untuk reaksi SN2 dari (S)-2-iodoheksana dengan nukleofil Natrium etoksida.
Tulis tahapan reaksi : Gambarkan (struktur 3-D) dari reaktan, intermediate, produk, nama
produk, diagram energi reaksi tsb.
2. Untuk reaksi 3-bromo-2-metilpentana dengan (CH3)3CO-K+
Berdasarkan substrat dan nukleofil tersebut, reaksi apa reaksi yang paling dominan (apakah
SN1, SN2, E1, E2). Tuliskan tahapan reaksi, produk dan namanya, diagram energy reaksi
tsb.
(Bobot 20%)

Organic chemistry 2014

Home work TOPIC 4 &5
1. For nucleophilic substitution reaction, compare a pair of nucleophiles in the below

problem. Which one has higher nucleophility. Give the reason.

a). (CH3)2N- atau (CH3)2NH
b). (CH3)3B atau (CH3)3N
c). H2O atau H2S
2. For nucleophilic substitution reaction, compare a pair of the below organo halogen,
which one is more reactive to nucleofil OHa) CH3Br atau CH3I
b). CH3CH2I in ethanol atau CH3CH2I in dimethylsulfoksida (CH3)2SO4
c). H2C=CHBr or H2C=CHCH2Br
3.Give an explanation why below reation is to follow SN2,SN1, E2, E1. Write and identify
the type of the substrate, transisi stansition state, product, including stereo (R/S
orientation), arrow of electron movement, and its energy diagram.
a).SN2 reaction of (S)-2-iodoheksana and CH3CH2S in dimethylsulfoksida as solvent
b).SN1 reaction of (1-bromo-1-metilpropil) benzene with H2O.
c).E2 reaction CH3)2CHCHBrCH2CH3 with potassium hydroxide
d).E1 reaction (1R,2R)-1,2-dibromo-1,2-difeniletana with KOH

HOMEWORK
1.

2.

Write structure of transition state, and product and energy diagram of the
reaction SN2 of OCH3 with
a). (S)-2-bromo-3-methylbutane
b).trans-1-chloromethyl-4-methylsiklokexane
Propose product of aqueous solvolysis of the following halide
c) cis-1-iodo-3-methylsiklohexane
d) (2R, 4S)-2-iodo-4-methykhexane

3.

Write structure of transition state, and product and energy diagram of the reaction
a). SN1 reaction of tert-bromo butana with water
b)E1 reaction tert-bromo butane with water
c) SN2 reaction bromo-propane with OHd) E2 reaction 2-bromopropane with OH-

TOPIC TEST CARBONIL COMPOUND

1. Reaction between aldehid and alcohol give hemiacetal which is only a minor component in a
mixture, except five or six ring member ring can form. Show the formation of cyclic hemiacetal
from 4-hydroxypentanal.
2. Show the mechanism of esterification using ACID CATALYST for the following reactant
( step by step formation of the protonized acid, intermediate, .etc.)

1. Transesterification reaction of triglyceride and methanol reactant can produce fatty ester
Show the mechanism of the transesterification using NaOH as catalyst ( step by step
formation of the metoxy, intermediate, fatty ester, diglyceride and monoglyceride
2. Below are compounds containing alcohol group and carboxyl group. If they give proton
(Brnsted acid) they become anion. The most stable anion would be given by compound
having the strongest acidity. Arrange the following compounds in order of decreasing acidity.

3. Ester compound can experience or undergo hydrolysis reaction. This reaction is the reverse of
esterification. Write the mechanism of basic hydrolysis of methyl ethanoate?

TEST TOPIC KARBOHIDRAT

1.
Glukosa adalah karbohidrat yang paling dekat dengan kehidupan sehari hari.
a).Gambarkan proyeksi Fischer D-glukosa rantai terbuka dan rantai tertutup -Dglukopiranosa dan -D-glukopiranosa (proyeksi Howard), melalui pembentukan
hemiasetal.
(Bobot 10%)
2.
Gambarkan pembentukan polisakarida amilosa dan selulosa dari Dari Dglukopiranosa, melalui ikatan 1, 4 glikosida,
(Bobot 10%)
3. Gambarkan dibawah adalah rumus kimia disakarida sukrosa atau dikenal sebagai gula,
Reaksi hidrolisa akan memutus ikatan glikosida gula oleh H 2O, menghasilkan dua
monosakarida. Apa nama kedua monosakarida tersebut dan tunjukkan reaksinya reaksi
hidrolisa dengan katalis basa OH(Bobot 10%)

TEST TOPIC PROTEIN

1. Diberikan 3 asam amino, dlm gambar samping. Tunjukkan tu mana Alanine,
Lysine atau Glutamate (dengan memberikan alasan), jika asam amino tersebut
bersifat sbb :
i) Lysine : polar, hydrophilic dan bermuatan (+),
ii) Aspartat : polar, hydrophilic, dan bermuatan (-)
iii) Alanine : non-polar aliphatic, hydrophobic dan
netral,
(Bobot 10%)
2. Dipeptida aspartam adalah N-(L--Aspartyl)-Lphenylalanine,1-methyl ester. Gambarkan struktur
senyawa ini dan tunjukkan ikatan peptidanya
(Bobot 10%)

3. Jika ASPARTAM dihidrolisa dengan basa NaOH, produk apa yang dihasilkan dan
tuliskan mekanisme reaksi hidrolisa tersebut.
(Bobot 10%)
4. Deretan asam amino dalam rantai polipeptida melalui ikatan peptida membentuk
struktur primer. Rantai polipeptida terpelintir membentuk spiral (-helix ) disebut
struktur sekunder, disebabkan oleh ikatan hidrogen antara CO dari asam amino ke1 dan hidrogen dari NH ke-4, Spiral polipeptida membengkok dan melipat disebut
struktur tertier, disebabkan oleh beberapa interaksi yaitu i) ikatan hidrogen
antara cabang polar, ii) ikatan ionik antara gugus R , iii) interaksi hidrofobik gugus
R non-polar, iv) jembatan disulfida (S-S). Tiga spiral polipeptida terpelintir
membentuk seperti tali (colagen), disebut struktur quarterner. Gambarkan
interaksi yang menyebabkan terjadinya struktur primer, sekunder, tertier dan
kuartetrner tersebut.
TEST TOPIC PROTEIN
Glukosa adalah karbohidrat yang paling dekat dengan kehidupan sehari hari, merupakan
golongan aldosa karena memiliki gugus hidroksi dan aldehida.. Gambarkan D-glukosa
struktur terbuka (proyeksi Fischer) dan perubahannya menjadi menjadi -Dglukopiranosa dan -D-glukopiranosa (proyeksi Howard) , melalui pembentukan
hemiasetal siklik (intramolekul).
2.Monosakarida D-glukopiranosa dapat membentuk disakarida dan polisakarida melalui
ikatan 1, 4 glikosida
a).Gambarkan pembentukan polisakarida amilosa dari D-glukopiranosa.
b) Gambarkan pembentukan polisakarida selulosa dari D-glukopiranosa
3. a) Asam asam amino memiliki sifat asam dan basa (ampoter) basa. Terangkan kenapa
demikian?.
b) Diberikan 3 struktur asam amino.seperti pada gambar. Pilihlah namanya yang tepat
diantara tiga nama dibawah dengan memberikan alasannya.(jawaban nebak tak diberikan
nilai)
i)Lysine, memiliki sifat polar, hydrophilic dan bermuatan (+)
ii)Alanine yang memiliki sifat non-polar aliphatic, hydrophobic da bermuatan netral
iii)Glutamate yang memiliki sifat polar, hydrophilic, dan bermuatan (-)

4. a). Protein terbuat dari satu atau lebih rantai polipeptida. Deretan asam amino dalam
rantai polipeptida melalui ikatan peptida membentuk struktur primer. Gambarkan
struktur primer yang dimaksud diatas untuk polipeptida dari alanine.
b).Rantai polipeptida terpelintir membentuk spiral (-helix ) disebabkan oleh ikatan
hidrogen antara CO dari asam amino ke-1 dan hidrogen dari NH ke-4. Gambarkan
interaksi yang terjadi pada pembentukan struktur sekunder yang dimaksud ini.
c) Kemudian rantai spiral polipeptida membengkok dan melipat (struktur tertier)
disebabkan oleh beberapa interaksi yaitu ) ikatan hidrogen antara cabang polar, ii)
ikatan ionik antara gugus R yang bermuatan (asam-basa), iii) interaksi hidropobik

gugus R non-polar, iv) jembatan disulfida (S-S) .Gambarkan interaksi yang dimaksud
tersebut.
d).Terbentuknya struktur quarterner, misalnya 3 polipeptida terpelintir membentuk
seperti tali (colagen) Gambarkan interaksi yang dimaksud ini.

ORGANIC CHEMISTRY FINAL TEST-a MEI 2013

CHEMICAL ENGINEERING DEPARTMENT FT-UI
Time: 70 menit, Lecturer: Dr.Ir.Sukirno M.Eng
------------------------------------------------------------------------------------------------1. Compare the nucleophility of CH3CH2S in dimethylsulfokside to that of CH3CH2S in
ethanol.
Give illustration how the solvent works. (10 point)
2. If (S)-2-iodoheksana is reacted with CH3CH2S in dimethylsulfoksida as solvent,
a).which pathways (SN2, SN1, E2, E1) is most likely to follow. Give analysis on the
substrate type, nucleophile reactivity, solvent type. (10 points)
b). Write the complete mechanism of the reaction, including the stereo (R/S
orientation) and electron movement of the reactant, the transition state and the
product. (20 poins)
c). Write energy diagram of the reaction and show the position the reactant, the
transition state and the product. (10 point)
3. By giving its proton, each of the below compounds can become an anion.
a). For each compounds, draw the anion and identify factor that stabilized it. (10
points)
b) Arrange them in order of stability . (5 points))
c) How does the stability of the anion correlate to the acidity of the compound that
produced the anion. Explain . (5 points)

4. Biodiesel can be made by transesterification reaction of trigliseride with methanol using

either acid catalyst or base catalyst. Write complete mechanism when
a). sulfuric acid is used as the catalyst. (15 points)
b). natrium hydroxide is used as the catalyst. (15 points)

ORGANIC CHEMISTRY FINAL TEST-b MEI 2013

CHEMICAL ENGINEERING DEPARTMENT FT-UI
Time: 70 menit, Lecturer: Dr.Ir.Sukirno M.Eng
------------------------------------------------------------------------------------------------1. Compare the nucleophility of CH3CH2O in ethanol to that of CH3CH2O in DMF
which abbreviation of N,N-dimethylformamide [HCON(CH3)2]
Give Lewis structure of the solvent and illustrate how they influence the reactivity of
the nuchleophile (15 point)
2. If (R)-2-iodoheksana is reacted with CH3CH2O in DMF as solvent,
a).which pathways (SN2, SN1, E2, E1) is most likely to be followed. Give analysis on
the substrate type, nucleophile reactivity, solvent type. (10 points)
b). Write the complete mechanism of the reaction, including the stereo (R/S
orientation) and electron movement of the reactant, the transition state and the
product. (15 poins)
c). Write energy diagram of the reaction and show the position the reactant, the
transition state and the product. (10 point)
3. By giving its proton, each of the below compounds can become an anion.
a). Draw the anion of each compound and show how it is stabilized by the resonance/
inductive effect. (10 points)
b) Arrange them in order of decreasing stability . (5 points))
c) How does the stability of the anion correlate to the acidity of the compound that
produced the anion. Explain . (5 points)

4. Typical substitution reaction of carboxyl group can be found in transesterification

reaction of triglyceride with ethanol to form diglyceride and fattyacid ethyl ester
(biodiesel).
Write the mechanism if
a). hydrochloric acid is used as the catalyst. (15 points)
b). potassium hydroxide is used as the catalyst. (15 points)
The mechanism should involves provocation step by catalyst, addition step and
elimination step

ORGANIC CHEMISTRY FINAL TEST-c MEI 2013

CHEMICAL ENGINEERING DEPARTMENT FT-UI
Time: 70 menit, Lecturer: Dr.Ir.Sukirno M.Eng
------------------------------------------------------------------------------------------------1. Compare the nucleophility of (C2H5)3O in ethanol to that of (C2H5)3O in DMA which
abbreviation of dimethylacetamide [CH3CON(CH3)2]
Give Lewis structure of the solvent and illustrate how they influence the reactivity of
the nuchleophile (10 point)
2. If (R)-1-methyl-2-bromopentana (C2H5)3CO in ethanol as solvent, at high temperature
a).which pathways (SN2 or SN1 or E2 or E1) is most likely to follow. Give analysis
on the substrate type, nucleophile reactivity, solvent type. (10 points)
b). Write the complete mechanism of the reaction, including the stereo (R/S
orientation) and electron movement of the reactant, the transition state and the
products. (20 poins)
c). Write energy diagram of the reaction and show the position the reactant, the
transition state and the product. (10 point)
3. By giving its proton, each of the below compounds can become an anion.
a). For each compounds, draw the anion and identify factor that stabilized it. (10
points)
b) Arrange them in order of decreasing stability . (5 points))
c) How does the stability of the anion correlate to the acidity of the compound that
produced the anion. Explain . (5 points)

5. Typical substitution reaction of carboxyl group can be found in transesterification

reaction of triglyceride with ethanol to form diglyceride and fattyacid ethylester
(biodiesel).
Write the mechanism if
a). hydrochloric acid is used as the catalyst. (15 points)
b). potassium hydroxide is used as the catalyst. (15 points)

HOMEWORK
1.

2.

Write structure of transition state, and product and energy diagram of the
reaction SN2 of OCH3 with
a). (S)-2-bromo-3-methylbutane
b).trans-1-chloromethyl-4-methylsiklokexane
Propose product of aqueous solvolysis of the following halide
e) cis-1-iodo-3-methylsiklohexane
f) (2R, 4S)-2-iodo-4-methykhexane

4.

a). SN1 reaction of tert-bromo butana with water

b)E1 reaction tert-bromo butane with water
c) SN2 reaction bromo-propane with OHd) E2 reaction 2-bromopropane with OH-

There are 1000 liters in one cubic meter. 22.4 liters of any gas is equal to 1 mole, according
to molar volume. Molar mass tells us that the main component of natural gas, methane,
or CH4, has a molar mass of 12+1+1+1+1, or 16g per mol. 16g/mol * 1000L/m3 / 22.4
L/mol = 714g/m3 = 0.714kg/m3 Therefore, there are 0.714 kilograms in a cubic meter of
natural gas.You must remember that this only applies under certain conditions. The 22.4
L/mol number is a result of the Ideal Gas Law PV=nRT. In order to equate volume with
moles, P and T must be specified (R is a constant). Only at atmospheric pressure (1atm)
and standard temperature (0 Celsius) is there 22.4 liters in a mole of gas.
PV=nRT
n=PV/RT
n2/n1=(P/T)2/(P/T)1
n2=(1.00/273+30)/(1/273)

ORGANIC CHEMISTRY FINAL TEST JUNE 2014

CHEMICAL ENGINEERING DEPARTMENT FT-UI
INTERNATIONAL PROGRAM
Time: 70 menit, Lecturer: Dr.Ir.Sukirno M.Eng
==============================================================
=

1. For this reaction

a).The above reaction would be expected to follow elimination reaction. E1 or
E2?, give explanation.
b).Write a complete mechanism of the reaction that shows how the compound
shown above would be expected to react.
c).Which is the major products, explain why.
d).Write the name the reactant and the products
2. Propose products of aqueous solvolysis (reaction with water)
(2R, 4S)-2-iodo-4-methylhexane
a) Write a complete SN1 mechanism
b) Write 3D structure of the reactant , transition state and products
c) Write the energy diagram of the reaction
3. Reaction of formaldehyde CH2O with urea CO(NH2)2 can produce polymer or
resin which is widely used as glue or binder
a) Write a mechanism of the formation of methylol urea as monomer
b) Write a mechanism of linier polymerization up to trimer
c) Is there any possibility of crosslinking to take place? If there is, show it.
4.

Write a complete mechanism of esterification when acetic acid is reacted

with ethanol
a) Using H2SO4 as catalyst
b) Using NaOH as catalyst

5.Recall your own mind map of organic compound, and write it down on your
answer sheet (2page)

ORGANIC CHEMISTRY FINAL TEST JUNE 2014

CHEMICAL ENGINEERING DEPARTMENT FT-UI
BIOPROCESS ENGINEERING PROGRAM
Time: 70 menit, Lecturer: Dr.Ir.Sukirno M.Eng
============================================================

1. For this reaction

a. The above reaction would be expected to follow elimination reaction. E1
or E2?, give explanation.
b. Write a complete mechanism of the reaction that shows how the
compound shown above would be expected to react.
c. Which is the major products, explain why
d. Write the name the reactant and the products
2. For substitution reaction of (S)-2-bromo-3-methylbutane with OCH 3
a) Write a complete mechanism of substitution reaction.
SN1 or SN2 ? Give explanation
b) Write the 3D structure of the reactant, transition state, and products
c) Write the energy diagram of the reaction

3. Reaction of formaldehyde CH 2O with melamin

can
produce polymer or resin which is widely used as glue or binder
a). Write a mechanism of the formation of the monomer resulted from
reaction of formaldehyde with melamine.
b). Write a complete mechanism of linier polimerization, up to trimer
c). Is there any possibility of crosslinking to take place? If there is, show it.
4. Write a complete mechanism of esterification when butyric acid is reacted
with ethanol
a) Using H2SO4 as catalyst
b) Using NaOH as catalyst
5. Recall your own mind map of organic compound, and write it down on
your answer sheet (2page)