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TUTORIAL 5
CHAPTER 5: ALKYL HALIDES
1.
2.
trans-1,2-dichlorocyclopentene
b)
3-chloro-4-phenylheptane
c)
1,2-dibromo-3-methylpentane
d)
1-Bromo-2,2-dimethylpropane
e)
trans-1,4-diiodocyclohexane
f)
1-bromo-3-methylhexane
g)
3-bromo-2,4-dimethylpentane
Br
b)
Cl
CH3
c)
Cl
CH3
d) (CH3)2CHCH2Br
e)
Br
Cl
f)
Cl
Cl
1
3.
Write the IUPAC names of the following alkyl halides, and classify them as
primary, secondary or tertiary alkyl halides.
a) CH3CH2CHFCH(CH3)2
b) (CH3)2CHCH2Cl
c) CH3CH2CHBrCH3
d) CH3CH2Cl
e) (CH3)3CBr
4.
CH3CH=CHCH3
CH3CH=CHCH2Cl
b)
CH3CH=CHCH3
CH3CHCHCH3
Br Br
c)
CH3C=CH2
Cl
Cl
CH3CCH3
Cl
d)
Br
5.
b)
2CH3CH2CH2 Cl
2Na
c) (CH3)2CHI + KCN
d) (CH3)2CHCH2CH2Cl +
CH3OH
NaH
6.
CH
d)
CH3
Cl
CH3
Br
b)
e)
CH3
CH3
Cl CH3
H3C CH CH2 C
Br
CH CH3
CH3
c)
CH3 CH3
CH3CHCBr
CH2CH3
7)
Predict the compound in each pair that will undergo the S N2 reaction
faster:
a)
Cl
or
Cl
b)
Cl
or
c)
Cl
d)
or
CH2Cl
or
Br
Br
e) CH3CH2CH2CH2Cl
or
CH3CH2CHCH3
Cl
8)
Draw the structure of the major product when the following compound
reacts with sodium hydroxide solution, NaOH, under reflux.
i)
CH3
H3C
CHCH2Br
ii)
CH3CH2CH2CH2Cl
iii)
CH3
H3C
Cl
CH3