ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.)
ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.)
3rd Edition
ISBN: 9781119497479
Author: Klein
Publisher: WILEY
Question
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Chapter 13, Problem 67IP

(a)

Interpretation Introduction

Interpretation:

The structure of the compound 2 has to be provided.

Concept introduction:

Sharpless asymmetric epoxidation: An Alkene containing a Hydroxyl group in the allylic position is called as Allylic alcohols. Allylic position is the position next to C=C bond.

ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.), Chapter 13, Problem 67IP , additional homework tip  1

Sharpless catalyst consists of Titanium tetraisopropoxide and one enantiomer of Diethyl tartrate (DET)

  ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.), Chapter 13, Problem 67IP , additional homework tip  2    ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.), Chapter 13, Problem 67IP , additional homework tip  3

A chiral complex is formed with Titanium tetraisopropoxide and with either +DET or -DET, and this complex serves as the chiral catalyst.

ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.), Chapter 13, Problem 67IP , additional homework tip  4

ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.), Chapter 13, Problem 67IP , additional homework tip  5

(b)

Interpretation Introduction

Interpretation:

The plausible mechanism for the transformation of 2to3 and the expected configuration at each of the chiral centers in 3 has to be proposed.

Concept introduction:

Ring-opening of epoxide:

The epoxide ring is highly strain and readily undergoes reaction with strong nucleophile result in the ring-opening reaction.

Base catalyzed ring opening of epoxide:

The nucleophile will attack at the less substituted position under basic conditions

(c)

Interpretation Introduction

Interpretation:

The structure of 4 has to be drawn.

Concept introduction:

Protection of alcohols as TMS Ethers:

The use of TMSCl and a base is used to form TMS ethers. Primary, secondary and tertiary alcohols can be silylated using TMSCl

Methanesulfonates also can be used as a protecting group for alcohols.

(d)

Interpretation Introduction

Interpretation:

The plausible mechanism for the transformation of 4 to 5 has to be drawn.

Concept introduction:

Deprotonation: The reaction in which proton is removed from the compound using reagents is known as deprotonation.

Nucleophile: donates pair of electrons to positively charged substrate resulting in the formation of chemical bond.

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Chapter 13 Solutions

ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.)

Ch. 13.5 - Prob. 9CCCh. 13.6 - Prob. 10CCCh. 13.7 - Prob. 11CCCh. 13.7 - Prob. 12CCCh. 13.8 - Prob. 3LTSCh. 13.8 - Prob. 13PTSCh. 13.8 - Prob. 14ATSCh. 13.9 - Prob. 15CCCh. 13.10 - Prob. 4LTSCh. 13.10 - Prob. 16PTSCh. 13.10 - Prob. 17ATSCh. 13.10 - Prob. 5LTSCh. 13.10 - Prob. 18PTSCh. 13.10 - The sequence below shows an enantioselective...Ch. 13.11 - Prob. 20CCCh. 13.11 - Prob. 21CCCh. 13.12 - Prob. 6LTSCh. 13.12 - Prob. 22PTSCh. 13.12 - Prob. 23ATSCh. 13.12 - Prob. 7LTSCh. 13.12 - Prob. 24PTSCh. 13.12 - Prob. 25ATSCh. 13 - Prob. 26PPCh. 13 - Prob. 27PPCh. 13 - Prob. 28PPCh. 13 - Prob. 29PPCh. 13 - Prob. 30PPCh. 13 - Prob. 31PPCh. 13 - Prob. 32PPCh. 13 - Methylmagnesium bromide reacts rapidly with...Ch. 13 - Prob. 34PPCh. 13 - Prob. 35PPCh. 13 - Prob. 36PPCh. 13 - Prob. 37PPCh. 13 - Prob. 38PPCh. 13 - Prob. 39PPCh. 13 - Prob. 40PPCh. 13 - Prob. 41PPCh. 13 - Prob. 42PPCh. 13 - Prob. 43PPCh. 13 - Prob. 44PPCh. 13 - Prob. 45PPCh. 13 - Prob. 46IPCh. 13 - Prob. 47IPCh. 13 - Prob. 48IPCh. 13 - Prob. 49IPCh. 13 - Prob. 50IPCh. 13 - Prob. 51IPCh. 13 - Prob. 52IPCh. 13 - Prob. 53IPCh. 13 - Prob. 54IPCh. 13 - Prob. 55IPCh. 13 - Prob. 56IPCh. 13 - Prob. 57IPCh. 13 - Prob. 58IPCh. 13 - Prob. 59IPCh. 13 - Prob. 60IPCh. 13 - Prob. 61IPCh. 13 - Prob. 62IPCh. 13 - Prob. 63IPCh. 13 - Prob. 64IPCh. 13 - Prob. 65IPCh. 13 - Prob. 66IPCh. 13 - Prob. 67IPCh. 13 - Prob. 68IPCh. 13 - Prob. 69IPCh. 13 - Prob. 70IPCh. 13 - The following procedure13 is part of a synthetic...Ch. 13 - Prob. 72CPCh. 13 - Prob. 73CPCh. 13 - Prob. 74CPCh. 13 - Prob. 75CP
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