Final January 2023 ‫الترم األول‬

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Chart Compound C8H10O

-Assign the IR spectrum

Wavenumber
Functional group

-Assign the NMR spectrum

-Structure of the compound

 Final January 2023 ‫الترم األول‬
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1) Which of the following compounds have proton with δ:3.7

a) b) c) d)none

2) the following compounds show n----->σ* except

a)Alcohol b)amines c)alkenes d)ether
3)the ratio of peaks of quartet signal is
a)1:3:3:1 b)1:2:1 c)1:4:6:4:1 d)none of them
4)which of the following compounds show M,M+2,M+4
a)1,2-dichlorocyclohexane b)1-bromo-2-chlorocyclohexane c)1,2-dibromocyclohexane d)1,2,3-tribromocyclohexane
5)number of signals in 1H-NMR of trans-1,2-dichlorocyclopropane
a)1 signals b)2signals c)3 signals d)4signals
6)

a) b)

c) d)

7)which of the following is the correct fragments for benzoic acid tropylium ion ‫مش متذكر االختيارات بالتحديد لكن المهم لم يكن يكون‬

a)m/z:77,105,121,94 b)m/z:77,105,121,91

b)m/z:76,105,121,95 d)77,120,95
8)compound C8H10O shows δ:2.25 (Singlet,3H) δ:3.81 (Singlet,3H) δ:6.81(d,2H) δ:7.10(d,2H)
a) 2,3-dimethylphenol b)p-methoxytoluene (p-methylanisole) c)m-methoxybenzaldhye d)p-methoxycyclohexane
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9)

a)2-hexanone b)3-hexanaone c)3-mehtyl-2-pentanone d)pentanal

10)

a)Ethanol b)Ethanal c)Ethanoic acid c)Ethylami

11)Compound shows in IR spectra bands in 3312,3150,2122,1600,

a) b)

c) d)

12)

Number of exocyclic double bonds a) 1 b) 2 c) 3 d) 4

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13) Increase in conjugation causes

a)Hypsochromic shift b)Bathochromic shift
c)Hyperchromic shift d)Hypochromic shift
14)compound have a proton appear at δ:3.41 with operating device 300MHz
what will be the δ with operating device of 600MHz
a)1.7 b)6.8 c)3.41 d)5.8
15) Number of signals in 1H-NMR

a)3 signals b)4 signals c)5 signals 4)6 signals

16)The multiplicity for this compound CH3CH2CH2NH2 in the following order
a)singlet,quintet,triplet,singlet b)triplet,quintet,triplet,singlet
c)triplet,sextet,triplet,singlet d) triplet,quintet,triplet,singlet
17)the order or increasing wavenumber for

a)4<1<2<3 b)1<4<3<2 c)1<4<2<3 d)4<1<3<2

18)the correct order for the following stretch

a)4>1>3>2 b)2>3>1>4 c)4>2>1>3 d)4>1>2>3

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Question three
1)compare between methyl salicylate and o-methoxy methylbenzoate (Which have lower wavenumber,comment)

2)Compare between 1-pentanol and pentanoic acid (C-O stretching,comment)

3)Compare between 1,2-butadiene and 2-methyl-2-butene and 1,4-butadiene (arrange C=C stretch,comment)

4) arrange the chemical shifts for the following protons

 Final January 2023 ‫الترم األول‬
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Draw the splitting digram for Hb

in case of

Jab=8Hz Jbc=4Hz Jab=4Hz Jbc=4Hz

Ha Hb
 Final January 2023 ‫الترم األول‬
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number of signals: number of signals:

Multiplicity of Ha: Multiplicity of Ha:

Multiplicity of Hb:

Draw the srtcture which gives in 1H-NMR singlet signals

C5H12 C4H6O2 C5H10

CH2=CH-CH2-CH2-CH3 [55,42,41]

Explain the fragment peaks of the following compounds

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Ph-COOCH2CH2CH3 [77,105,122]

Which of the following compounds represent its mass spectrum

2-methyl-3-pentanone 2-Hexanol 3-Hexanol
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Draw the fragment at m/z=45

The structure is

Draw the fragment at m/z=59

The structure is

Predict the stucture from the 1H-NMR data

a)C5H8O3 δ: 12.2(Singlet,1H) δ: 2.65 two overlapping triples(4H) δ:2.10(Singlet,3H)

b) C7H12O4 δ: 4.11(q,4H) δ: 3.21(s,2H) δ: 1.20(t,6H)

C)

-What type of the proton diastereotopic(D) enantiotopic(E) Neither(N)

 ‫الترم األول ‪Final January 2023‬‬
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‫‪Calculate the λmax‬‬

‫و في النهاية ’’‪‘’No matter what keep move forward‬‬

‫الرحِ ِيم‬
‫حْم ِن ه‬ ‫الر َٰ‬
‫َّللا ه‬
‫س ِم ه ِ‬ ‫بِ ْ‬
‫علَى النَّبِي ِ َيا أَيُّ َها الَّذِينَ آ َمنُوا‬‫َ‬ ‫ونَ‬ ‫ُّ‬ ‫ل‬‫ص‬ ‫ي‬ ‫) ِإ َّن َّ‬
‫ّللا َو َمال ِئ َكتَهُ ُ َ‬
‫س ِل ُموا ت َ ْسلِي ًما(‬ ‫صلُّوا َ‬
‫علَ ْي ِه َو َ‬ ‫َ‬