Introduction to Strategies for Organic Synthesis by Laurie S. Starkey

By Laurie S. Starkey

This booklet will reveal the best way to synthesize aim molecules (TMs) that
contain a number of useful teams (FGs), comparable to C≡C (alkyne), OH (alcohol
or carboxylic acid), and C=O (aldehyde, ketone, and lots of others). The process
of making plans a synthesis, referred to as a retrosynthesis, is without doubt one of the most crucial tools
within the “toolbox” had to resolve synthesis difficulties. the strategy of retrosynthetic
analysis is brought during this bankruptcy and is used all through the
book. this primary bankruptcy also will evaluation using protecting teams (PGs) in
organic synthesis. the second one bankruptcy offers extra valuable instruments needed
by the start synthesis scholar through reviewing universal nucleophiles and
electrophiles, in addition to a few normal reagents for oxidation and reduction

Show description

Read or Download Introduction to Strategies for Organic Synthesis PDF

Best organic books

Advanced Organic Chemistry: Part A: Structure and Mechanisms

In view that its unique visual appeal in 1977, complicated natural Chemistry has maintained its position because the most popular textbook within the box, delivering wide insurance of the constitution, reactivity and synthesis of natural compounds. As within the past variations, the textual content comprises wide references to either the first and assessment literature and gives examples of information and reactions that illustrate and record the generalizations.

Protective Groups in Organic Chemistry

In past times decade there was an exceptional elevate within the use of protecting teams, in particular within the synthesis of huge and complicated natural molecules. probably the best task has been within the peptide box the place such triumphs because the overall synthesis of insulin and of bovine ribonuclease (molecular weight 13,700) were completed.

Protein Purification: Principles and Practice

The 3rd variation of this vintage advisor to protein purification updates tools, ideas and references. As within the widely-acclaimed past variants, Scopes publications either the beginner and the skilled researcher from conception to program. utilizing the booklet, the reader is ready to combine tools successfully into optimal protocols for the duty to hand.

Additional info for Introduction to Strategies for Organic Synthesis

Sample text

Treatment of an alkene with ozone creates an ozonide intermediate that breaks down upon workup. A “reductive” workup uses a reducing agent, such as zinc or dimethylsulfide (DMS, CH3SCH3). If there were any hydrogens attached to the original C=C double bond, they are preserved in a reductive workup, and aldehyde products would be formed. The use of NaBH4 in the workup reduces the carbonyls formed in situ, affording alcohol products. If an “oxidative” workup were used instead, the added oxidizing agent (H2O2) would replace any aldehyde C–H bonds with C–O bonds to give carboxylic acid products.

Common Electrophiles Electrophile (E+) Name Example of Product with Nu: C carbocation δ+ δR X alkyl halide R-Nu O δδ+ epoxide Nu δ+ δO ketone or aldehyde δ+ Cannot put carbocation in a bottle! Instead, E+ reagents typically have δ+ sites. C Nu X = Cl, Br, I OH Nu OH Nu "1,2-addition" O of Nu: "1,4-addition" of Nu: δ+ δ+ α,β-unsat'd ket/ald (enone) OH 1,2-add'n Nu: = LiAlH4, RMgX, RLi O Nu: = enolate, cuprate, N, O 1,4-add'n (Michael) Nu δ+ O C O carbon dioxide (CO2) O Nu OH O R δ+ OR ester Nu O R δ+ Cl carboxylic acid derivatives generally add two equiv.

O3; 2. H2O2 ozonolysis with reductive workup or dihydroxylation/oxidation gives aldehyde(s) R' R OH O O R R' ozonolysis with oxidative workup gives carboxylic acid(s) Ozonolysis of Alkenes Oxidation of Alkynes Upon oxidation of an alkyne, the C≡C triple bond can be cleaved completely. All three C–C bonds are oxidized to form three new C–O bonds, resulting in carboxylic acid products. This oxidation can be carried out either by ozonolysis or with KMnO4 (dihydroxylation occurs, followed by additional oxidative cleavage).

Download PDF sample

Rated 4.76 of 5 – based on 3 votes