JIMMA UNIVERSITY

CHEMISTRY DEPARTMENT
Organic Chemistry
Worksheet I
1. Classify the following molecules as polar or nonpolar. For molecules which are polar indicate the electron
distribution pattern. Determine also the type of intermolecular force (s) potentially to exist within each
molecules

h)
i) (CH3)3N j) CH3SOCH3 k) CH3CH3 l) CH2CH2

2. Determine hybridization of each atom (or those coded as 1, 2 or asterisk () in the following molecules?
O
A) H2C CH C CH B) H3C C OH C) CH2 CH2 CH CH3 D) H2C CH CH2

O O
CH3CCH2CH2CCH2CH2CH2COH
CH2
E) F) G) H)
3. Identify the type of orbital overlap which is responsible for formation of bonds labeled 1-6 (for A) expected
bond angles labeled A-E (for B) 5
4
H H
5 2 1 A B C D E
3
H3C C C C C C
H
NH
H
H2N C NH CH2 C N
(A) (B)
4. Draw all reasonable resonance forms for the structures shown below. Use curved arrows to indicate
Electron pair changes. If possible decide which one is the major resonance contributors.
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D) CH3 C O CH E) CH HN C N
3 3
A) B) C) CH3NO2 O
5. Draw any alternative structural representations possible (Lewis-dot, Lewis-Kekule, Line/zigzag or
Condensed) and molecular formula for each of the following molecules

D) CH3CN E) CH3NO2

F) G) H) CH3CO2CH2CH3 I) J)

K) L) M) N)

6. For each of the following molecule. Determine the

a. Type of functional groups they contained (show each of the functional groups you identified by
encircling)
b. Total number of sigma and Pi- bonds
c. Molecular formula and estimated M.wt
d. Degree of unsaturation and
e. Number of chiral centers

(A) (B) (C) (D) (E)

(F) (G) (H)

(E)
7. Methanol (CH3OH; bp = 65°C) boils nearly 230° higher than methane (CH4; bp = ‐164°C), but 1‐decanol
(C10H21OH; bp = 229°C) boils only 55° higher than decane (C10H22; bp =174°C). Explain.

8. Which should have the higher boiling point, methanol (CH3OH) or bromomethane (CH3Br)? Why?
9. Identify each of the following alkyl groups as being primary, secondary or tertiary and give the IUPAC
name

10. Give the IUPAC name for the following compounds by including appropriate stereochemical notations when
ever important.
CH3 CH3
CHCH2CHCH3 Cl
H3CH2C
B) C) D)
A)

E) F) H)
G) H3C

C) Br
D)
CH3 CH
CH2 CH CH2 CH
3

I) J) OH K) L)

M) N) O) P) Q)

B)

R) S) T) U) V)

W) X) Y) Z)

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 d)
c) IUPAC
OH OH OH
MgBr
CH2 CH CH CH2 CH3
a) b)
f) g)
h)
e)

OH
CH2
i) j) k) l)

m) n) q)
o) p)

r) s)

11. Draw the structure which corresponding to the following systematic names.
a) Cis-3,3-Dimethyl-4-propyl-1,5-octadiene b) 4-Methyl-1,2-pentadiene
c) trans-2,2,5,5-Tetramethyl-3-hexene d) 1-Isopropyl-4-methylcyclohexene
e) 4-methyl-1,2-pentadiene f) (4E)-2,4-Dimethyl-1, 4-hexadiene
g) Bicyclo[2.1.0]pentane h) 2-Chlorobicyclo[3.2.0]heptane
i) 1-Ethyl-1-phenylcyclopropane j) 3-Methyl-1,2-butadiene
k) Isopropylbenzene (or 2-phenylpropane) l) m-Bromobenzaldehyde
m) 1, 8-Dichloronaphthalene n) 2,5-Dichlorotoluene
o) p-(t-Butyl)phenol p) o-Nitrotoluene
q) Hexafluorobenzene r) 3, 5-Dibromostyrene
s) Phenylallyl etherEthyl benzoate t) 2,2-Dimethyloxirane(2-Methyl-1,2-epoxypropane)
u)  - Bromo--methylbutanal v) 1,2,3-Butanetriol
w) 4-Oxopentanoic acid x) 2,5-Dioxaheptane
y) 2-(2,4- Dichporophenoxy)propanoic acid z)3,5-Dihydroxy-3-methylpentanoic acid
A) m-Chlorobenzoyl bromide B) 1,3-Diphenyl-2- propanone
C) Acetic propionic anhydride D) Diethyl malonate
E) 2-Heptanone F) 1-Octanol
G) Acrolein H) 2,2-butyldiamine
I) N,N-dimethylpropaneamide

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12. Using Newman projection draw each of the following molecules in its most stable conformation with
respect to the bond indicated

13. Draw the most stable chair conformation of the following compounds.
CH3 CH3

C CH3
C CH3
H3C CH3
H3C CH3
14. For each of the following cyclohexane derivatives, indicate (i) Whether the molecule is a cis or trans
isomer and (ii) whether it is the most stable conformation

15. Rank the following sets of substituents in order of priority according to the Cahn –Ingold-Prelog
sequence rules.
, ,
a) COOH , COOCH3 CH2OH CH3
b) HC CH2 , CN , CH2NH2 , CH2Br
c) HC CH2 , CH2CH3 , CH2OCH3 , CH2OH
16. Identify whether configuration for the following compounds is (E) or (Z) and complete naming

CH3
O
H CH2Cl H3C N CH
O 2 C N
HO
HO
C CH3 H3C O CH2
CH3 Cl HC CH2
H3C

(A) (B) (C)

17. Identify whether the following compounds are chiral or achiral.

(a) 2-Methylheptane (b) 3-Methylheptane (c) 4-Methylheptane
(d) 1,1-Dibromopropane (e) 1,2-Dibromopropane (f) 1,3-Dibromopropane
(g) 2-chloropentane (h) 1-chloro-2-methylpentane (i) 1-chloropentane
CH3
Br CH3 O CH3

j) H3C k) H3C CH3

l) H3C
O m) H3C
O

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18) Draw enantiomers of the following compounds (if any).

i) BrIFCH ii) ClF2CH iii) CH3-CH(NH2)-CO2H

19) Draw and name all possible isomers of CH3CHBrCHClCH3. Describe also the relationship which exists
among them.

20) Consider the following pairs of structures. Identify the relation between them (Constitutional isomers,
Enantiomers, Diastereomers, Conformers, Geometric isomers, Identical molecules or not related at all).
If they are stereoisomers specify the configuration and configuration involved.

CH3 CH3 CH3 H

H Br H Br Br H H3C Br
(i)
A) and (j)B) and
HO H
HO H H OH H3C OH

CH3 CH3 H CH3

CH3 CH3 CH3 CH3

H
H H H
C) H and H3C (l) D) H3C and H H
(k) H H
H H H H
CH3 H H H
CH3

(m)
(n)

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21) Assign the appropriate designation of configuration (R or S) to the stereocenter in each of the following
enantiomers. (Hint: Regarding cyclic structures containing stereocenters, treat the ring as if it were two
separate substituents that happen to be attached to each other at the far end of the molecule — look for the
first point of difference, just as you would for acyclic structures.)

CHO
CO2H CO2H
H3CH2C H
Cl C H H C CH3 HO H
HC CH2 OH CH3
CH2OH

22) Draw structural representations of each of the following molecules. Be sure that your structure clearly
shows the configuration at the stereocenter. (Hint: You may find it useful to first draw the enantiomer
whose configuration is easiest for you to determine and then, if necessary, modify your structure to fit the
one requested in the problem.)
(a) (R)-2-chloropentane (b) (S)-2-methyl-3-bromohexane
(d) (R)-2-chloro-1,1,1-trichloro-3-methylbutane. (c) (S)-1,3-dichlorobutane

(e ) (1R,2R,3S)-1,2-dichloro-3-ethylcyclohexane (f) (3R,5S)-3,5-dimethylheptane

(g) (2R,3S)-2-bromo-3-methylpentane (h) (S)-1,1,2- trimethylcyclopropane
(i) (1S,2S)-1-chloro-1-tri"fluoromethyl-2-methylcyclobutane (j) (R)-3-bromo-3-methylhexane