Show reagents and experimental conditions to synthesize the following compounds from 1-propanol (any derivative of 1-propanol prepared in one part of this problem may be used for the synthesis of another part of the problem). (a) Propanal (b) Propanoic acid (c) Propene (d) 2-Propanol (e) 2-Bromopropane (f) 1-Chloropropane (g) 1,2-Dibromopropane (h) Propyne (i) 2-Propanone (j) 1-Chloro-2-propanol (k) Methyloxirane (1) Dipropyl ether (m) Isopropyl propyl ether (n) 1-Mercapto-2-propanol (o) 1-Amino-2-propanol (p) 1,2-Propanediol

Short Answer

Expert verified
(d) 2-Propanol #tag_title#Step 1: Reduction of 2-propanone to 2-propanol #tag_content#To synthesize 2-propanol from 1-propanol, we first need to prepare 2-propanone using the steps outlined for (i) 2-Propanone. Once 2-propanone is obtained, carry out a reduction reaction using sodium borohydride (NaBH4) in a suitable solvent, such as methanol (MeOH). The reaction proceeds as follows: 2-propanone + NaBH4 → 2-propanol + NaBH3 (e) 2-Bromopropane #tag_title#Step 1: Substitution of 2-propanol to 2-bromopropane #tag_content#First, prepare 2-propanol using the steps outlined for (d) 2-Propanol. Then, to synthesize 2-bromopropane from 2-propanol, we need to perform a substitution reaction using hydrobromic acid (HBr) in water as the solvent. The reaction proceeds as follows: 2-propanol + HBr → 2-bromopropane + water

Step by step solution

01

Oxidation of 1-propanol

To synthesize propanal from 1-propanol, we need to oxidize 1-propanol using an appropriate oxidizing agent. A suitable oxidizing agent is pyridinium chlorochromate (PCC) in dichloromethane as a solvent. The reaction occurs as follows: 1-propanol + PCC → propanal + reduced PCC (b) Propanoic acid
02

Oxidation of 1-propanol to propanal

As mentioned in part (a), oxidize 1-propanol using pyridinium chlorochromate (PCC) to obtain propanal.
03

Oxidation of propanal to propanoic acid

To convert propanal to propanoic acid, we need to further oxidize it. Use potassium permanganate (KMnO4) in an aqueous solution and heat the reaction mixture to achieve this transformation. The reaction proceeds as follows: propanal + KMnO4 → propanoic acid + reduced KMnO4 (c) Propene
04

Dehydration of 1-propanol to propene

To synthesize propene from 1-propanol, we need to dehydrate 1-propanol. To do this, heat 1-propanol in the presence of concentrated sulfuric acid (H2SO4) and distill the reaction products to isolate propene formed as a gas. The reaction proceeds as follows: 1-propanol + H2SO4 → propene + water For the rest of the steps, please refer to the reactions and reagents identified in Phase 1. These will guide you in constructing the appropriate step-by-step synthesis for each target molecule, as illustrated in the examples provided for (a), (b), and (c).

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