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CHM1206 Worksheet 6 Solutions
CHM1206 Worksheet 6 Solutions
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
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
3-methyl-2-propylpent-1-ene 2-butyne
3-phenyl-butyne hepta-3,6-dien-1-yne
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
2-chloro-1,1-dimethylcyclopentane
cis-1,2-diethylcyclopropane
trans-1,ethyl-2-methylcyclohexane or
1,1-dimethylcyclobutane cyclobutylcyclopentane
1-iodo-4-chlorocyclohexane
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
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.