[Notsmartenough]

That example is in exercise 10 from Chapter 6 in Clayden Organic Chemistry. Unfortunately in a Solutions Manual this particular reaction was omitted. I suppose the product will be 5-chloro-2-hydroxy-5-methylhexanenitrile.

On the other hand I do not know if "HCl" written under the rxn arrow means either there is only a quantity to "neutralize" NaCN into HCN and NaCl added, or we should be considering electrophilic addition as a secondary reaction?

[AWK]

Without heating, the hydrolysis of nitrile does not take place

[Notsmartenough]

Last question what about addition of HCl to the double bond? I suppose HCl is just to create more reactive HOCl, but I might be wrong.

[AWK]

Last question what about addition of HCl to the double bond?
I suppose HCl is just to create more reactive HOCl, but I might be wrong.

1. Did you use a dry HCl?
2. You are wrong. Elemental chlorine with water forms a mixture of HCl and HOCl.

[Notsmartenough]

Last question what about addition of HCl to the double bond?
I suppose HCl is just to create more reactive HOCl, but I might be wrong.

1. Did you use a dry HCl?
2. You are wrong. Elemental chlorine with water forms a mixture of HCl and HOCl.

My mistake, I was thinking about HCN not HOCl. (NaCN + HCl)

According to dry HCl, are you suggesting the reaction of an alkene with hydrogen halide will not occur in aqueous phase?

[AWK]

This is two steps reaction - the addition of CN- and neutralization.

[Notsmartenough]

So the double bond stays untouched, and the product is just a cyanohydrin. Thank you for your help.