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).

7. Arrange the following series of substituents in order of increasing E/Z prioritywhere 1 = lowest and 4 = highest priority.

a)

b)

8. 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,

2. 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 Brønsted 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.

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

+

6. Untuk species kimia berikut : i)CO32- ii) SH2 iii) NH2

1- iv) NO21+ v) O3

a) (10 poin) Berikan struktur Lewisnyab) (10 poin) Berikan hibridasi atom yang digaris bawahic) (10poin) muatan formal atom yang digaris bawahi

7. Urutkan substituent berikut menurut naiknya prioritas E/Z

(a) (b) (c) (d)

8. Stability (think heat of hydrogenation):

(a) (b) (c) (d)

9.

What is the hybridization of the oxygen atom in water?What is the molecular geometry for ammonia (NH3)? What is the electron-pair geometry of the central oxygen atom of ozone (O3)? Which of the following molecules does not have a net dipole moment?

a) H2O , NH3, BF3 , BrF5 The individual boron-fluorine bonds are very polar due to the electronegativity difference between these two atoms. However, boron is sp2 hybridized and has a trigonal planar molecular and electron-pair geometry. Trigonal planar geometry places the three fluorine atoms in the same plane at 120o bond angles. All of the individual dipoles will cancel each other out for a net molecular dipole of zero.

TOPIC : STRUCTURE CHEMICAL REACTION

ADDITION1. Ramalkan produk yang diperoleh

2. Give the stepwise mechanism for the following reaction. Use arrows to indicatethe 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.

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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

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 esterShow the mechanism of the transesterification using NaOH as catalyst ( step by step formation of the metoxy,

intermediate, fatty ester, diglyceride and monoglyceridea) 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 & aspirinb). 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

benzene + ch2chch3 + hf

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)

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 aCHEMICAL 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 bCHEMICAL 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)2NHb). (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 OH-

a) CH3Br atau CH3Ib). CH3CH2I dalam etanol atau CH3CH2I dalam dimethylsulfoksidac). H2C=CHBr atau H2C=CHCH2Br

3.Berikan penjelasan kenapa mengikuti SN2,SN1, E2, E1 (berdasarkan substrat, nukleofil, leaving group, pelarut). Tuliskan reaktan, transisi, intermediate, 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