1) 3-methylbutan-1-ol undergo oxidation with PDC reagent to form 3-methylbutanal as major product. Overoxidation to acid with this reagent is not possible with this mild oxidizing reagent.
2) Cyclopentanone is reduced with sodium borohydride to form cyclopentanone
3) Ketone group of 1-phenylbutan-1-one is protected with ethanol to form (1,1-diethoxybutyl)benzene as major product.
4) octan-4-one react with diethyl amine to form imine (Z)-N,N-diethyloct-3-en-4-amine with cis and trans compound
5) 2-hydroxybenzaldehyde reacts with Grignard reagent to form 2-(1-hydroxy-3-methylbutyl)phenol as major product. Here excess of Grignard is needed as 1 mole of Grignard will be quenched by acidic phenolic proton.
6) 2,3-dimethylpent-1-ene react with cobalt catalyst in presence of CO and H2 to form 3,4-dimethylhexanal as major product.

OH + PDC CH2Cl2 + NaBH, + * HOCH.CH HCI/EVOH + NH(CH3)2 CHE MgBr Et, +...
1. CH MgBr 2. HO 1. (CH3),Cuti 2. H2O 1. CHg MgBr 2. H20 1. (CH3)2NH 2. H20 2. H20 1. CH CHANH, OCH,CHE 2 HO CH OH • Sul
O + CH3-NH2 H,SO4 HHH+ CH-CoH heat CH3 CH3-C-Cl- + CH3-CH-OH CH3 CH3 CH3-C-OH + CH3-CH-MgBr CH3 CH3-c-o-CH, -. Et,0 soch CH-OH
6. CH3 Br CCI 7. CH3 Br CH, OH 8. CHE 1. MCPBA 2. CH,OH, H* 9. CH Oso,,H,O, 10. Na, NH 0
Classify each of the following organic reactions. Addition CH3-CH2-CH-CH3 – CH3-CH2-CH=CH2 + HCI CH3-C-O-CH3 + CH3-NH-CH3-C-NH-CH3 + CH2-OH CH3-CH2-CH2-OH + HBr -- CH3-CH2-CH2-Br + H20 Elimination OH CH2-CH + HCN – CH3-CH-CN CH3-CH=CH-CH3 + HBr + CH3-CH-CH2-CH3 Br Substitution CH3-CH2-CH2-CH3 + Cl2 → CH-CH2-CH2-CH3 + HCI СІ CH3-CH=CH-CH3 + Cl2 - CH3-CH-CH-CH3 CICI Reset
Write balanced and net equations
NiCl2 + Na2CO3 NiCl2 + NH Br Ba(OH)2 + HCI Ba(OH)2 + NaCO3 Ba(OH)2 + NH Br HCl + Na.Co HCl + NH Br Na,CO, + NH Br
NICH NANO/HCI NH <5°c N(CH3 -N(CH3)2 (CH3)N N(CH3)2 ON N(CH3)2
-NH2 PCC, CH2Cl2 NaBH CN OH 8 Br 1. 3 equiv. 12 4 equiv. NaOH 1. LiAlH4 2. H2O 2. H30* 9 10 2 equiv. (CH3)2NH 1. LiAIH 2. H20 11 12 H2O 1. CH,MgCI 2. H30 13 14
Do problem 19.34 on pg. 741. Phenyl acetaldehyde acetophenone SH CH₃ NaBH. then H30 Tollen's Reagent NH,OH, HCI catalyst CH,MgBr, then H,O* 2 CH,OH, HCI catalyst H2NNH, KOH (CH)-ch, HCN/ KCN
Hg(OAc), CH,OH Mola), CHOMME NaBHA 1) BH/THF (2)-3-hexene 2) H202/OH CH3 Br2 CH2Cl2 (solvent) - CH2 CH2Cl2 (solvent) Cl2 ch H2O CH3 1) CH,COH 2) H30 20) PhCOH CH2Cl2 (solvent) CH3 OSOA H202 CH3 1) 03 2) (CH3)2S KMnO4 (hot, conc.)
Select (more than one) steps
OH PCC NaBHA CH3OH 1. MgBr CH2Cl2 EtOH H 2. H H2 OH HO HCN DCC KCN