CHM1206- INTRODUCTION TO INORGANIC AND ORGANIC CHEMISTRY

TUTORIAL WORKSHEET 6 2022/2023

Alkenes

What is the IUPAC name of the following compounds?

CH2 =C(CH3)CH2CH2CH3 2-methylpent-1-ene

CH3CH2CH=C(CH3)2 2-methylpent-2-ene

(CH3)2CHC(CH3)=CHCH3 3,4-dimethylpent-2-ene

(CH3)2C=CHCH2CH(CH3)2 2,5-dimethylhex-2-ene

(CH3)3CCH=C(CH3)CH2CH3 2,2,4-trimethylhex-3-ene

CH3CHClCH2CH=CHCH2CHCl2 2,2,6-trichlorohept-3-ene

HC≡CCH2CH2CH3 pent-1-yne
(CH3)2C(CH2CH3)C≡CCH(CH3)2 2,2,5-trimethylhept-3-yne
BrCH2CH2CCCH2CH3 1-bromohex-3-yne

Draw the structural formula for the following compounds

Cis-2-butene 2-ethylbut-1-ene

2,4,6,6-tetramethylhept-2-ene
2,3-dimethyl-1-butene 2,3,3-trimethyl-1-butene

4,4-dimethyl-2-pentene trans 4-ethyloct-3-ene

3-methyl-2-propylpent-1-ene 2-butyne

3-phenyl-butyne hepta-3,6-dien-1-yne

Determine which of the following compounds show cis-trans isomerism.

CH3CH=CH2

CH3CH=CHCH2CH3

CH3CH=CHCH3

hex-3-ene

buta-1,3-diene

hexa-2,4-diene

3-methylpent-2-ene

2,3-dimethylpent-2-ene

3,4-dibromocyclopentene
For the given cycloalkanes, write their formulae, draw the structure and fill their
predicted bond angles. Evaluate their stability by comparing the bond angles with that of
sp3 bond angle

Cyclopropane Cyclobutane Cyclopentane

Formula C3H6 C4H8 C5H10
Structure
Bond angle 60 90 108
Stability Unstable, 60<<109.5 Unstable 90<<109.5 stable

Name the compounds shown below

Draw structures for the following compounds

2-chloro-1,1-dimethylcyclopentane

cis-1,2-diethylcyclopropane

trans-1,ethyl-2-methylcyclohexane or

1,1-dimethylcyclobutane cyclobutylcyclopentane
1-iodo-4-chlorocyclohexane

Stereochemistry, optical activity

Draw the stereoisomers of these compounds:

1,3-Dimethylcyclohexane

1-Chloro-3-methylcyclopentane

Carbons bonded to 4 different substituents are called stereogenic centers. Name the
following compounds and find the stereogenic centers, if any.
For each compound, determine whether the molecule has an internal mirror plane of
symmetry. If it does, draw the mirror plane on a three-dimensional drawing of the
molecule. If the molecule does not have an internal mirror plane, determine whether or
not the structure is chiral.
methane mirror, achiral

cis-1,2-dibromocyclobutane mirror, achiral

trans-1,2-dibromocyclobutane chiral, no mirror

1,2-dichloropropane chiral, no mirror

chiral, no mirror

Draw the enantiomers of 1,3-dibromobutane and label them as (R) and (S).

Star each asymmetric carbon atom in the following examples, and determine whether it
has the (R) or (S) configuration
Treat the alkene carbon
atom as bonded to two
carbon atoms by representing
the double bond as two
single bonds. This causes the
alkene to have more substituents
than the carbon atom in substituent 2.

1 2
3 C

1
1 2 2

3
C
Anticlockwise 3
R but assigned S R
as R because
H atom is above anticlockwise;
the plane. imagine looking from
the bottom side
When one of the enantiomers of butan-2-ol is placed in a polarimeter, the observed
rotation is 4.05° counterclockwise. The solution was made by diluting 6.00 g of butan-2-
ol to a total of 40.0 mL, and the solution was placed into a 200-mm polarimeter tube for
the measurement. Determine the specific rotation for this enantiomer of butan-2-ol.

A solution of 2.0 g of (+)-glyceraldehyde, HOCH2-CHOH-CHO, in 10.0 mL of water was

placed in a 100-mm cell. Using the sodium D line, a rotation of +1.74° was found at 25
°C. Determine the specific rotation of (+)-glyceraldehyde.