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Problem Set 5
1. Name the following alkyl halides according to the IUPAC system.
(Remember to use R/S designations if appropriate!)
2. Name the following "simple" alkyl halides using common nomenclature.
Cl (^) F Br iso-butyl chloride (^) hexyl fluoride (^) t-butyl bromide
3. Classify each halo compound shown below as an alkyl, vinyl or aryl halide. Also:
§ If the compound is an alkyl halide, indicate whether it is 1°, 2° or 3°; and also if it is allylic or
benzylic.
§ Circle any organic halide below that can undergo a SN1 or SN2 type substitution reaction.
Cl Cl 1 - chloro- 2 - methylpropane ( 2 R, 3 R, 6 S)- 2 chloro, 8 ethyl, 3 , 6 dimethyl decane Cl Br Cl
I
F
Br
I
Br F alkyl, 1 o, SN 2 allylic 3 o, SN 1 3 o, SN 1 allylic 2 o, SN 1 or SN 2 alkyl, 1 o, SN 2 benzylic, 1 o, SN 2 2 o, SN 1 or SN 2 vinyl aryl (phenyl)
4. Draw the products of the following substitution reactions. If the organic halide shown is not
reactive under the conditions shown, simply write N.R. (no reaction).
Br
+ OH
Cl
NH 2
I
+ SCH 3
Br + CH 3
Cl + C C CH 3
I H^3 C
O
O
OH
+ Br
NH 2
+ Cl
+ Br
+ I
No
reaction
No
reaction
O
O
6. Complete the following reactions by drawing the intermediate charged substitution product
and the neutral final organic product. Be sure to draw out the mechanisms for both steps.
Br charged organic intermediate neutral organic product
H 2 O
(solvent) NH 3 ( 2 eq) charged organic intermediate neutral organic product Cl (^) Et 2 O Methanol charged organic intermediate neutral organic product Cl charged organic intermediate neutral organic product
I H 2 N^ (^2 eq)
DMF
O
H
H
OH
H 2 O
+ H 3 O+
NH 3
N
H
H
H
+ NH 4 +
NH 2
CH 3 OH
O
H
H H
2 N^
N
H
H 3 N
7. Draw the products of the following SN2 reactions:
(c) In the space below draw a stepwise, detailed mechanism for the reaction in part (a).
8. Draw the neutral organic products of the following SN1 reactions:
I CH
3 OH^ OH
(a) (b) Et CH 3 iPr Br H 2 O
OCH 3
OCH 3
Et (^) CH 3 iPr OH
(c) In the space below draw a stepwise, detailed mechanism for the reaction in part (a).
I
CH 3 OH
OCH 3
OCH 3
+ I
attack possible from both sides
H
H
I
I
OCH 3
OCH 3
+ HI
Br (^) CH 3 O
- H 3 C^ Cl NaCN (a) (b) OCH 3
- Br H 3 C CN
- NaCl Br CH 3 O-^ OCH^3
- Br
