Without consulting the Reaction Road Map on page 1009, suggest reagents that convert each of the following starting materials into the indicated product: 

(a) (chloromethyl)- benzene (benzyl chloride) into phenylmethanamine (benzylamine); 

(b) benzaldehyde into phenylmethanamine (benzylamine); 

(c) benzaldehyde into N-ethylphenylmethanamine (benzylethylamine); 

(d) (chloromethyl)benzene (benzyl chloride) into 2-phenylethanamine (phenethylamine); 

(e) benzaldehyde into N,N-dimethylphenylmethanamine (benzyldimethylamine); 

(f) 1-phenylethanone (acetophenone) into 3-amino-1-phenyl-1-propanone; 

(g) benzonitrile into phenylmethanamine (benzylamine); 

(h) 2-phenylacetamide into phenylmethanamine (benzylamine). 

Map on page 1009

Transcribed Image Text:

R H(R') R H(R') 'N' R R RR H(R") RNO. R" H(R") RČNH: RC=N RBr Zn(Hg), HCI H(R') or H* or OH, R'NH, H-N H(R") H*, HO R'NH, LIAIH, H,, Ni or Fe, HCI X2, NaOH LIAIH, H;0, A Other Product: Product: OH product: Other R-C-NHR" c-c- Substrate: product: RCOOH Product: R=aryl R R R" R'HN H RNH2 16-5 17-9 17-9 18-9 20-6 20-6 20-7 20-8 21-5 H(R') C-N H(R") 21-5 21-6 21-9 22-4, 26-5 22-4 25-2 25-6 26-2 Product: NH, Product: Product: Product: Product: Product: Product: R H(R') RNH NHR NH, R'-C-N H(R") R'CCHR R' ČH,N H(R") NO: R-C-CN Nu NH2 H. NO, NO, CH;=0, H, R' HN H(R') H-N H(R") NANH, liquid NH3 LIAIH RNH2 -NH2 : Nu NH3, HCN NaBH,CN H(R") RN3 R R'CCH,R NO, R R2 R H. NO,