Question

Predict the products of the following reactions:

1. $\mathbf{\text{butan-2-one\hspace{0.17em}\hspace{0.17em}}}\mathbf{+}\mathbf{\text{\hspace{0.17em}\hspace{0.17em}diethylamine}}\stackrel{{\mathbf{\text{NaBH(OAc)}}}_{\mathbf{\text{3}}}}{\mathbf{\to }}$
   
2. $\mathbf{\text{4-fluoropyridine}}\stackrel{{\mathbf{\text{NaOCH}}}_{\mathbf{\text{2}}}{\mathbf{\text{CH}}}_{\mathbf{\text{3}}}}{\mathbf{\to }}$
   
3. $\mathbf{\text{3-nitroaniline}}\underset{\mathbf{\text{(2)CuBr}}}{\overset{{\mathbf{\text{(1)HCl,NaNO}}}_{\mathbf{\text{2}}}}{\mathbf{\to }}}$
   
4. $\mathbf{\text{butan-2-one}}\underset{{\mathbf{\text{(2)LiAlH}}}_{\mathbf{\text{4}}}}{\overset{\mathbf{\text{(1)KCN,HCN}}}{\mathbf{\to }}}$
   
5. $\mathbf{\text{cyclopentanone}}\underset{{\mathbf{\text{(2)LiAlH}}}_{\mathbf{\text{4}}}}{\overset{{\mathbf{\text{(1)aniline,H}}}^{\mathbf{\text{+}}}}{\mathbf{\to }}}$
   
6. $\mathbf{\text{2-bromopentane}}\underset{{\mathbf{\text{(2)Ag}}}_{\mathbf{\text{2}}}\mathbf{\text{O,heat}}}{\overset{{\mathbf{\text{(1)(CH}}}_{\mathbf{\text{3}}}{\mathbf{\text{)}}}_{\mathbf{\text{3}}}\mathbf{\text{N:}}}{\mathbf{\to }}}$
   
7. 
   

h.

i.

j.

Short answer

a.

b.

c.

d.

e.

f.

g.

h.

i.

j.

Step-by-step solution

Prediction of products

(a) Butan-2-one reacts with diethylamine in presence of sodium triacetoxyborohydride to give the final product as N,N-diethylbutan-2-amine.

reaction a

(b) 4-fluoropyridine on treatment with sodium ethoxide gives the product as 4-ethoxypyridine.

reaction b

(c) 3-nitroaniline on treatment with hydrochloric acid and sodium nitrite followed by copper bromide gives the final product as 3-bromoaniline.

reaction c

(d) Butan-2-one on treatment with potassium cyanide and hydrogen cyanide gives the initial product as 2-hydroxy-2-methylbutanenitrile, which on further eduction with lithium aluminum hydride gives the final product as 1-amino-2-methylbutan-2-ol.

reaction d

(e) Cyclopentanone reacts with aniline in presence of an acid to give the initial product as N-cyclopentylideneaniline, , which on further eduction with lithium aluminum hydride gives the final product as N-cyclopentylaniline.

reaction e

(f) 2-bromopetane on treatment with trimethylaniline gives the initial product as N,N,N-trimethylpentan-2-aminium, which on further treatement with silver oxide followed by heating gives the final products as pent-1-ene and trimethylamine.

reaction f

(g) Cyclohexanone on treatment with ethylamine in presence of an acid followed by the loss of a water molecule gives the product as N-cyclohexylideneethanamine.

reaction g

(h) Cyclohexanone on treatment with diethylamine followed by reduction with sodium triacetoxyborohydride gives the product as N-ethylcyclohexanamine.

reaction h

(i) The given compound on treatment with hydrogen peroxide followed by heating gives the product as 3,3-dimethylcyclohex-1-ene.

reaction i

(j) The given compound on treatment with excess methyl iodide followed by another treatment with silver oxide and heating gives the product as as shown below.

reaction j