16-06-10 Assorted Organic Candy

And finally, a bonus question -:
Q6. I have with me Br-(CH2)4-OH. I have to transform it into HO-(CH2)4-COOH. I can do this by the Grignard method(CO2) and by the Cyanide method(substitution and then hydrolysis). Which will work and which will not?

7 Answers

39
Pritish Chakraborty ·

No one trying these? :O
Except ankur..

106
Asish Mahapatra ·

r these correct ?

39
Pritish Chakraborty ·

Yo

1
Ankur ·

Bravo cool! Someone saved me from painting figures. :P

39
Pritish Chakraborty ·

Answers -:

Q2. HIO4 has no effect on trans diols, and can oxidize only cis diols. Pb(OAc)4 oxidizes both types of diols, and hence the answer is a diketone in the second reaction, and no reaction occurs in the first.

Q3. It is a simple directed aldol condensation followed by ozonolysis. I won't list all the products here, but the final product is 2-oxo-cyclohexanone.

Q4. Addition of HCN across C=O, reduction of -CN to -CH2-NH2 and the rest is easily found out. The final product is a six membered ketone.

Q5. Five membered ring forms here. Silver causes the reaction to proceed forward. Find out yourself.

1
Sonne ·

oh nice one pritish !

i remember now the transition state of oxidation of diols using HIO4 cannot go for trans like position
it will become highly strained

1
Ankur ·

:O @Pritish: Yeah, Q2 was really short.. foolish me!

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