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Magazine Chapter 11: Q21P (page 562)
Give the structures of the products you would expect when each alcohol reacts with
(1) HCl, ZnCl2; (2) HBr; (3) PBr3; (4) P/I2; and (5) SOCl2.
(a) butan-1-ol (b) 2-methylbutan-2-ol
(c) 2,2-dimethylbutan-1-ol (d) cis-3-methylcyclopentanol
Short Answer
(a) 
(b) 
(c) 
(d) 
Step by step solution
Step 1: butan-1-ol reaction with given reactant to form the products
- Butan-1-ol is primary alcohol; it reacts with Lucas reagent (HCl/ZnCl2) very slowly Because the activated primary alcohol cannot form a carbocation. It remains in solution until the chloride ion attacks it, forming the product 1-chloro butane.
Butan-1-ol is the primary alcohol that reacts with HBr by the SN2 mechanism to form product 1-bromo butane.
Butan-1-ol is the primary alcohol reacting it with Phosphorus tribromide is often the best reagent for converting it into primary alkyl bromide, thus forming product 1-Bromo butane.
Butan-1-ol is the primary alcohol reacting it with phosphorus/iodine combination (P/l2) is often the best reagent for converting it into primary alkyl iodide, thus forming product 1-iodobutane.
Butan-1-ol is the primary alcohol reacting it with thionyl chloride (SOCl2) convert it into alkyl chloride, naming 1-chlorobutane.
Products formed when reacting with butan-1-ol
2-methyl butane-2-ol reaction with given reactant to form the products
- 2-methyl butane-2-olis secondary alcohol; it reacts with Lucas reagent (HCl/ZnCl2) for about 1 to 5 minutes because their secondary carbocations are more stable than primary ones forming the product 2-chloro-2 methyl butane.
2-methyl butane-2-olis secondary alcohol that reacts with HBr by the SN1 mechanism to form product 2-bromo-2 methyl butane.
2-methyl butane-2-olis secondary alcohol; it reacts with Phosphorus tribromide and converts into secondary alkyl bromide, thus forming product 2-bromo-2 methyl butane.
2-methyl butane-2-olis secondary alcohol reacting it with phosphorus/iodine combination (P/l2) is often the best reagent for converting it into secondary alkyl iodide, thus forming product 2-iodo-2 methyl butane.
2-methyl butane-2-olis secondary alcohol reacting it with thionyl chloride (SOCl2 ) convert it into alkyl chloride, naming 2-chloro-2 methyl butane.
Products formed when reacting with 2-methyl butane-2-ol
2,2-dimethylbutan-1-ol reaction with given reactant to form the products
- 2,2-dimethylbutan-1-olis primary alcohol; it reacts with Lucas reagent (HCL/ZnCl2 ) very slowly Because the activated primary alcohol cannot form a carbocation. It remains in solution until the chloride ion attacks it, forming the product 3-chloro-3methyl pentane.
2,2-dimethylbutan-1-olis the primary alcohol that reacts with HBr by the SN2 mechanism to form a product mixture of products 1-bromo 2,2- dimethyl butane, and 3-bromo-3-methyl pentane
2,2-dimethylbutan-1-ol is the primary alcohol reacting it with Phosphorus tribromide is often the best reagent for converting it into primary alkyl bromide, thus forming product1-bromo 2,2- dimethyl butane.
2,2-dimethylbutan-1-ol is the primary alcohol reacting it with phosphorus/iodine combination (P/l2 )is often the best reagent for converting it into primary alkyl iodide, thus forming product 1-iodo-2,2-dimethyl butane.
2,2-dimethylbutan-1-ol is the primary alcohol reacting it with thionyl chloride (SOCl2 ) convert it into alkyl chloride, naming 1-chlo-2,2-dimethyl butane.
Products formed when reacting with 2,2-dimethylbutan-1-ol
cis-3-methylcyclopentanol reaction with given reactant to form the products
- cis-3-methylcyclopentanolis secondary alcohol; it reacts with Lucas reagent (HCl/ZnCl2 ) for about 1 to 5 minutes because their secondary carbocations (chloride ion attack from either side ) are more stable than primary ones forming the mixture of products (1S,3R)-1-chloro-3-methyl cyclopentaneand(2S,5S)-2-chloro-5-methyl cyclopentane-1-ylium.
cis-3-methylcyclopentanolis secondary alcohol that reacts with HBr by the SN1 mechanism to form a mixture of products (1S,3R)-1-bromo-3-methyl cyclopentaneand(2S,5S)-2-bromo-5-methyl cyclopentane-1-ylium.
cis-3-methylcyclopentanolis secondary alcohol; it reacts withPhosphorus tribromide and converts into secondary alkyl bromide, thus forming product(1R,3R)-1-bromo-3-methyl cyclopentane.
cis-3-methylcyclopentanolis secondary alcohol reacting it with phosphorus/iodine combination (P/l2 ) is often the best reagent for converting it into secondary alkyl iodide, thus forming product (1R,3R)-1-iodo-3-methyl cyclopentane.
cis-3-methylcyclopentanolis secondary alcohol reacting with thionyl chloride (SOCl2 ) convert it into alkyl chloride, naming (1S,3R)-1-chloro-3-methyl cyclopentane.
Products formed when reacting with cis-3-methylcyclopentanol
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