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Question: Predict the products of the following reactions:

(a)

(b)

(c)

Short Answer

Expert verified

(a)

(b)

(c)

Step by step solution

01

Step-by-Step SolutionStep 1: Preparation of alcohols

Alcohols can be prepared from many other compounds like alkene, aldehydes, ketones, alkyl halides and esters. The methods used for preparing alcohols from alkenes are hydration, oxymercuration-demercuration and hydroxylation of alkene.

02

The product of the reaction in (a)  

(a) In the given reaction, hydroboration of alkene takes place. The oxidation of alkene occurs, which yields syn, and the hydration product formed is non-Markovnikov. This means the hydroxyl group is bonded to that carbon which is less substituted.

Preparation of alcohol

03

The product of the reaction in (b)

(b) In the given reaction, oxymercuration-demercuration of alkene takes place. The given alkene is treated with , and then the product is treated with . The hydration product is formed by the Markovnikov rule, which means the hydroxyl group is bonded to that carbon of alkene, which is more substituted.

Preparation of alcohol

04

The product of the reaction in (c)

(c) In the given reaction, hydroxylation of alkene takes place. The given alkene is treated with and followed by reduction with . A meso-5,6-Decanediol (cis diol) is formed, which has syn stereochemistry.

Preparation of alcohol

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Most popular questions from this chapter

2,3-Dimethyl-2,3-butanediol has the common name pinacol. On heating with aqueous acid, pinacol rearranges to pinacolone, 3,3-dimethyl-2-butanone. Suggest a mechanism for this reaction.

Benzyl chloride can be converted intobenzaldehyde by treatment with nitromethane and base. The reactioninvolves the initial conversion of nitromethane in to its anion, followed by SN2 reaction of the anion with benzyl chloride and subsequent E2 reaction. Write the mechanism in detail, using curved arrows to indicate the electron flow in each step.

Benzyl chloride Nitromethane anion Benzaldehyde

A compound of unknown structure gave the following spectroscopic data:

Mass spectrum:M+=88.1

IR: 3600 cm-1

1HNMR: 1.4δ (2H, quartet, J=7Hz); 1.2δ (6H, singlet); 1.0δ (1H, singlet); 0.9δ (3H, triplet, J=7Hz)

13CNMR: 74, 35, 27, 25δ

(a) Assuming that the compound contains C and H but may or may not contain O, give three possible molecular formulas.

(b) How many protons (H) does the compound contain?

(c) What functional group(s) does the compound contain?

(d) How many carbons does the compound contain?

(e) What is the molecular formula of the compound?

(f) What is the structure of the compound?

(g) Assign peaks in the molecule’s NMR spectrum corresponding to specific protons.

Starting from testosterone (Problem 17-62), how would you prepare the following substances?

a.

b.

c.

d.

Dehydration of trans-2-methylcyclopentanol with POCl3 in pyridine yields predominantly 3-methylcyclopentene. Is the stereochemistry of this dehydration syn or anti? Can you suggest a reason for formation of the observed product? (Make molecular models!)

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