QUIS II

ORGANIC CHEMISTRY I
1. Draw all products, including stereoisomers, in each reaction. (Presensi
no 2 Muhammad Taufiq Fauzi)

2. Draw the products formed when each compound is treated with

CH3CH2COCl, AlCl3. (Presensi no 3 Umi Rusiyani)

3. Give the expected major product(s) of each of the following reactions.

(Presensi no 4 Itsna Husni Fajri)

4. Show the resonance of intermediate structures of aniline,

benzaldehyde, and phenol in electrophilic aromatic substitution.
(Presensi no 5 Hamzatul Munir)
5. Although alcohol V gives a single alkene W when treated with POCl3
and pyridine, three isomeric alkenes (XZ) are formed on dehydration
with H2SO4. Draw a stepwise mechanism for each reaction and explain
why the difference occurs. (Presensi no 6 Putri Kusuma Ramadhani

6. Which of the following heterocycles are aromatic? (Presensi no 7

Helah)

7. Give the product (or products) that you would expect to be formed in
each of the following reactions. In each case give the mechanism (SN1,
SN2, E1, or E2) by which the product is formed and predict the relative
amount of each (i.e., would the product be the only product, the major
product, or a minor product?). (Presensi no 8 Mariam Novianti)

8. Your task is to prepare isopropyl methyl ether by one of the following

reactions. Which reaction would give the better yield? Explain your
answer. (Presensi no 9 Mita Sulistia)

9. Which product (or products) would you expect to obtain from each of
the following reactions? In each part give the mechanism (SN1, SN2,
E1, or E2) by which each product is formed and predict the relative
amount of each product (i.e., would the product be the only product,

the major product, a minor product, etc.?). (Presensi no 10 Fitria Ayu

Nugraheni (a-f) dan presensi no 11 Wulantika Virginia (g-k))

10.
Although ethyl bromide and isobutyl bromide are both primary
halides, ethyl bromide undergoes SN2 reactions more than 10 times
faster than isobutyl bromide does. When each compound is treated
with a strong base/nucleophile (EtO-), isobutyl bromide gives a greater
yield of elimination products than substitution products, whereas with
ethyl bromide this behavior is reversed. What factor accounts for these
results? (Presensi no 12 Wening Oktaviani)
11.
Write mechanisms that account for the products of the following
reactions: (Presensi no 13 Auna Fany Nor)

12.
In contrast to SN2 reactions, SN1 reactions show relatively little
nucleophile selectivity. That is, when more than one nucleophile is
present in the reaction medium, SN1 reactions show only a slight
tendency to discriminate between weak nucleophiles and strong
nucleophiles, whereas SN2 reactions show a marked tendency to
discriminate.
(a) Provide an explanation for this behavior.
(b)Show how your answer accounts for the following:

(Presensi no 14 Andriana)
13.
Show how you might carry out the following transformations:
(Presensi no 15 Alfianisa Fadhilla)

14.
What compounds would you expect to be formed when each of
the following ethers is refluxed with excess concentrated hydrobromic
acid? (Presensi no 16 Yuni Astuti)

15.
Considering AL to represent the major products formed in each
of the following reactions, provide a structure for each of A through L.
If more than one product can reasonably be conceived from a given
reaction, include those as well. (Presensi no 17 Reni Rantika (A-F)
dan presensi no 18 Nurul Septiana (G-L))

16.
Predict the major product from each of the following reactions.
(Presensi no 19 Erly Lestari)

17.
Predict the products from each of the following reactions.
(Presensi no 19 Erly Lestari (a-e) dan presensi 20 Imam Aditya
Ramadhan (f-j))

18.
Which oxidizing or reducing agent would you use to carry out the
following transformations? (presensi no 21 Ely Puspita Sari)

19.
Predict the organic product from each of the following oxidation
reactions. (presensi no 22 Rezky Fazryatu M)

20.
Provide the reagents needed to accomplish transformations (a)
(g). More than one step may be necessary. (presensi no 23 Retno
Prapti Utami)

21.
Predict the organic product from each of the following oxidation
and reduction reactions. (presensi no 24 Rinta Nur Ariyani)

22.
Predict the organic product from each of the following reduction
reactions. (presensi no 25 Herlina Wijayanti)

23.
Which of the following molecules would you expect to be
aromatic? (presensi no 26 Fatkhiyatul Fitri (a-f) dan presensi 27
Andika Setyana)

24.
Write the structure of the product formed when each of the
following compounds reacts with one molar equivalent of HCl.
(presensi no 28 Afiyatul Futhona)

25.
Provide a detailed mechanism for each of the following reactions.
Include contributing resonance structures and the resonance hybrid for
the arenium ion intermediates. (presensi no 29 Tika Rahmawati)

26.
Predict the major product (or products) formed when each of the
following reacts with Cl2 and FeCl3: (presensi no 30 Zakiyatul
Habibah Oktavi)
(a) Ethylbenzene
(b) Anisole (methoxybenzene)
(c) Fluorobenzene
(d) Benzoic acid
(e) Nitrobenzene
(f) Chlorobenzene
(g) Biphenyl (C6H5-C6H5)
(h) Ethyl phenyl ether
27.
Predict the major product (or products) formed when each of the
following reacts with a mixture of concentrated HNO3 and H2SO4.
(presensi no 31 Hemarita Rayuni Nurgita)

28.
What monobromination product (or products) would you expect
to obtain when the following compounds undergo ring bromination with
Br2 and FeBr3? (presensi no 32 Nur Azizah Jamil)

29.
Starting with benzene, outline a synthesis of each of the
following: (presensi no 33 M. Khotibul Umam (a-e), presensi no 34
Rovik (f-i), dan presensi 35 Inas Fathimah (j-m)
(a) Isopropylbenzene
(b) tert-Butylbenzene
(c) Propylbenzene
(d) Butylbenzene
(e) 1-tert-Butyl-4-chlorobenzene
(f) 1-Phenylcyclopentene
(g) trans-2-Phenylcyclopentanol

(h) m-Dinitrobenzene
(i) m-Bromonitrobenzene
(j) p-Bromonitrobenzene
(k) p-Chlorobenzenesulfonic acid
(l) o-Chloronitrobenzene
(m) m-Nitrobenzenesulfonic acid
30.
Starting with toluene, outline a synthesis of each of the following:
(presensi no 36 Nila Asmila Sari (a-c), 37 Anis Ma'rifatul
Mustofiyah (d-f), 38 Bani Hafidz Nazali (g-j))
(a) m-Chlorobenzoic acid
(b) p-Methylacetophenone
(c) 2-Bromo-4-nitrotoluene
(d) p-Bromobenzoic acid
(e) 1-Chloro-3-trichloromethylbenzene
(f) p-Isopropyltoluene (p-cymene)
(g) 1-Cyclohexyl-4-methylbenzene
(h) 2,4,6-Trinitrotoluene (TNT)
(i) 4-Chloro-2-nitrobenzoic acid
(j) 1-Butyl-4-methylbenzene
31.
Starting with aniline, outline a synthesis of each of the following:
(presensi no 39 Romjah)
(a) p-Bromoaniline
(b) o-Bromoaniline
(c) 2-Bromo-4-nitroaniline
(d) 4-Bromo-2-nitroaniline
(e) 2,4,6-Tribromoaniline
32.
Furan undergoes electrophilic aromatic substitution. Use
resonance structures for possible arenium ion intermediates to predict
whether furan is likely to undergo bromination more rapidly at C2 or at
C3. (presensi no 40 Najid Azma)

33.
Propose structures for compounds GH: (presensi no 41 Benny
Yanuar Dwi Satrio)

34.
How can you explain the fact that trans-1-bromo-2methylcyclohexane yields the non-Zaitsev elimination product 3methylcyclohexene on treatment with base? (presensi no 42
Suryanti)

35.
Predict the product and give the stereochemistry resulting from
reaction of each of the following nucleophiles with (R)-2-bromooctane:
(presensi no 43 Efendi)
(a) -CN (b) CH3CO2- (c) CH3S36.
Propose a mechanism to account for the following reaction:
(presensi no 44 Siti Nuryani)

37.
How would you synthesize the following compounds from
benzene? Assume that ortho and para isomers can be separated.
(presensi no 45 Samrotul Ilmi)

38.
Draw resonance structures of the intermediate carbocations in
the bromination of naphthalene, and account for the fact that
naphthalene undergoes electrophilic substitution at C1 rather than C2.
(presensi no 46 Fatihah Husniyah)

39.
At what position, and on what ring, would you expect the
following substances to undergo electrophilic substitution? (presensi
no 47 Nahdliyah Amalia)

40.
What product(s) would you expect to obtain from the following
reactions? (presensi no 48 Yan Rahmad Al Fajri)

41.
Predict the major product(s) of the following reactions: (presensi
no 49 Sri Wahyuni Setiyaningsih)

42.
As written, the following syntheses have flaws. What is wrong
with each? (presensi no 50 Kunti Abqoria Hisan Hirtsa)

Selamat Mengerjakan
Sukses untuk UAS nya
(^_^)
10. Meskipun etil bromida dan isobutil bromida keduanya halida primer, etil bromida
mengalami reaksi SN2 lebih dari 10 kali lebih cepat dari isobutil bromida. Ketika
masing-masing senyawa diperlakukan dengan basa yang kuat / nukleofil (ETO-),
isobutil bromida memberikan hasil yang lebih besar pada produk eliminasi daripada
produk substitusi, sedangkan dengan etil bromida perilaku ini dibalik. Apa faktor
menyumbang hasil ini?
Tersubstitusinya lebih cepat metil > etil > isopropyl

faktor sterik
metil molekulnya lbih kecil < etil < isobutil .jadi efek steriknya lebih kecil dibanding keduanya .
shg rx substitusi menjadi lebih cepat.

Karena reaksi SN2 melibatkan reaksi biomolekuler sebagai langkah awal. Serangan belakang
harus melalui halangan sterik pertama

Naiknya laju reaksi SN2

Dengan bertmbahnya jumlah gugus alkil yang terikat pada karbon ujung (CH3X 1. + 2.
3.), keadaan transisinya bertambah berjejal dengan atom. Perhatikan contoh berikut dari reaksi
alkil bromida dengan ion metoksida (CH3O-) sebagai nuklofil (CH3O- + RBr CH3OR + Br-),
yang ditunjukkan. Jejealan ruang dalam sturktur-struktur disebut rintangan sterik (steric
hindrance). Bila gugus-gugus besar berjejalan dalam suatu ruang sempit, tolak-menolak antara
gugus bertambah parah dank arena itu energy system tinggi. Dalam suatu reaksi SN2 energi
suatu keadaan transisi yang berjejal lebih tinggi daripada energy keadaan transisi dengan
rintangan sterik pindah. Karena inilah maka laju reaksi makin menurun dalam deret metil,
primer, sekunder dan tersier.

Seperti substrat, halangan sterik mempengaruhi kekuatan nukleofil ini. The metoksida anion,
misalnya, adalah suatu dasar yang kuat dan nukleofil karena merupakan nukleofil metil, dan
dengan demikian sangat banyak tanpa hambatan. tert-butoksida, di sisi lain, adalah basa kuat,
tapi nukleofil miskin, karena kelompok metil tiga menghambat pendekatan untuk karbon.
Kekuatan nukleofil juga dipengaruhi oleh biaya dan elektronegativitas: nucleophilicity
meningkat dengan meningkatnya muatan negatif dan penurunan elektronegativitas. Sebagai
contoh, OH-adalah nukleofil yang lebih baik daripada air, dan saya-adalah nukleofil yang lebih
baik daripada Br-(dalam pelarut protik polar). Dalam aprotik pelarut polar, nucleophilicity
meningkat hingga kolom tabel periodik karena tidak ada ikatan hidrogen antara pelarut dan
nukleofil, dalam hal ini nucleophilicity cermin kebasaan. I-karena itu akan menjadi nukleofil
lemah dari Br-karena itu adalah dasar lemah. Putusan - Sebuah nukleofil kuat / anionik selalu
nikmat SN2 cara substitusi nucleophillic.

SN2 reaksi umumnya disukai di alkil halida primer atau sekunder alkil halida dengan pelarut
aprotik. Mereka terjadi pada tingkat tersier diabaikan dalam alkil halida karena halangan sterik.
Reaksi samping yang umum terjadi dengan SN2 reaksi adalah eliminasi E2: anion yang masuk
dapat bertindak sebagai basis daripada sebagai nukleofil, abstrak proton dan mengarah ke
pembentukan alkena. Ini lebih umum ketika ion masuk sterik dalam hal abstrak proton jauh lebih
mudah. Efek ini dapat ditunjukkan dalam reaksi fase gas antara sulfonat dan bromida alkil
sederhana mengambil tempat di dalam spektrometer massa
Dengan etil bromida, produk reaksi didominasi produk substitusi. Seperti sterik hambatan di
sekitar pusat meningkat elektrofilik, seperti isobutil bromida, substitusi disfavored dan eliminasi
adalah reaksi dominan. Faktor-faktor lain mendukung eliminasi adalah kekuatan basa. Dengan
substrat benzoate kurang basa, isopropil bromida bereaksi dengan 55% substitusi. Secara umum,
reaksi fase gas dan reaksi fase solusi jenis ini mengikuti tren yang sama, meskipun di pertama,
efek pelarut dieliminasi.