Pre Reactivity of Alkyl Halides
Reactivity’s of Some Alkyl Halides- SN2 & SN1
A. Johnson
8/28/12
CHM236
Objective: To test the ten compounds found in the physical data table that follows, and observe them by categorizing the reactions as Sn1 and SN2.
Physical data:
Compound M.W. (g/mol) Melting Point (C°) Boiling Point (C°) Density (g/mL) Solubility Safety Considerations
2-chlorobutane 92.57 -140 68 0.87 very slightly soluble in cold water Irritant with skin, lung, and eyes.
2-bromobutane 137.03 -112 91.2 1.25 Irritant with skin, lung, and eyes.
1-chlorobutane 92.57 -123 79 0.88 insoluble in water, miscible with ETOH Irritant with skin, lung, and eyes.
1-bromobutane 137.03 -112.4 101.4 1.2676 Insoluble in water
2-chloro-2methylpropane 92.57 -25 51.5 0.87 n/a crotyl chloride 90.55 -65 73 0.9491 insoluble in cold water benzyl chloride 126.59 -43 179 1.1 partially soluble in diethyl ether/methanol, insoluble in water bromobenzene 157.02 -30.6 156.2 1.495 soluble in methanol/diethyl ether bromocyclohexane 163.06 -56.5 166 1.3604 insoluble in water bromocylopentane 149.04 n/a 137 insoluble in water
Sodium Iodine in acetone 149.89 661 1304 3.67 soluble in acetone/ETOH
Silver Nitrate in ethanol 169.87 212 444 4.35 soluble in water
Calculations & Chemical Reactions:
Sample Table:
Compound Name SN1 SN2 Time for precipitant
2-chlorobutane y Y
2-bromobutane y Y
1-chlorobutane Y
1-bromobutane Y
2-chloro-2methylpropane
crotyl chloride benzyl chloride bromobenzene bromocyclohexane bromocyclopentae Procedure: For both procedures, you will need a 50 ̊ C water bath
□ fill a 100 mL beaker half full with water,
□ place it on a hot plate and heat it until the water is 50-55 ̊ C.
If the bath becomes too hot, you can periodically lower the temperature by adding some ice or cool water to the bath.
SN2
□ Place about 0.1 mL of each of the halides in small labeled test tubes.
A. Johnson
8/28/12
CHM236
Objective: To test the ten compounds found in the physical data table that follows, and observe them by categorizing the reactions as Sn1 and SN2.
Physical data:
Compound M.W. (g/mol) Melting Point (C°) Boiling Point (C°) Density (g/mL) Solubility Safety Considerations
2-chlorobutane 92.57 -140 68 0.87 very slightly soluble in cold water Irritant with skin, lung, and eyes.
2-bromobutane 137.03 -112 91.2 1.25 Irritant with skin, lung, and eyes.
1-chlorobutane 92.57 -123 79 0.88 insoluble in water, miscible with ETOH Irritant with skin, lung, and eyes.
1-bromobutane 137.03 -112.4 101.4 1.2676 Insoluble in water
2-chloro-2methylpropane 92.57 -25 51.5 0.87 n/a crotyl chloride 90.55 -65 73 0.9491 insoluble in cold water benzyl chloride 126.59 -43 179 1.1 partially soluble in diethyl ether/methanol, insoluble in water bromobenzene 157.02 -30.6 156.2 1.495 soluble in methanol/diethyl ether bromocyclohexane 163.06 -56.5 166 1.3604 insoluble in water bromocylopentane 149.04 n/a 137 insoluble in water
Sodium Iodine in acetone 149.89 661 1304 3.67 soluble in acetone/ETOH
Silver Nitrate in ethanol 169.87 212 444 4.35 soluble in water
Calculations & Chemical Reactions:
Sample Table:
Compound Name SN1 SN2 Time for precipitant
2-chlorobutane y Y
2-bromobutane y Y
1-chlorobutane Y
1-bromobutane Y
2-chloro-2methylpropane
crotyl chloride benzyl chloride bromobenzene bromocyclohexane bromocyclopentae Procedure: For both procedures, you will need a 50 ̊ C water bath
□ fill a 100 mL beaker half full with water,
□ place it on a hot plate and heat it until the water is 50-55 ̊ C.
If the bath becomes too hot, you can periodically lower the temperature by adding some ice or cool water to the bath.
SN2
□ Place about 0.1 mL of each of the halides in small labeled test tubes.