Skip to main content
Chemistry LibreTexts

Appendix II: Review of laboratory synthesis reactions

  1. Last updated
  2. Save as PDF
  • Page ID
    395045

    \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} } \)

    \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash {#1}}} \)

    \( \newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\)

    ( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\)

    \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\)

    \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\)

    \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\)

    \( \newcommand{\Span}{\mathrm{span}}\)

    \( \newcommand{\id}{\mathrm{id}}\)

    \( \newcommand{\Span}{\mathrm{span}}\)

    \( \newcommand{\kernel}{\mathrm{null}\,}\)

    \( \newcommand{\range}{\mathrm{range}\,}\)

    \( \newcommand{\RealPart}{\mathrm{Re}}\)

    \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\)

    \( \newcommand{\Argument}{\mathrm{Arg}}\)

    \( \newcommand{\norm}[1]{\| #1 \|}\)

    \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\)

    \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\AA}{\unicode[.8,0]{x212B}}\)

    \( \newcommand{\vectorA}[1]{\vec{#1}}      % arrow\)

    \( \newcommand{\vectorAt}[1]{\vec{\text{#1}}}      % arrow\)

    \( \newcommand{\vectorB}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} } \)

    \( \newcommand{\vectorC}[1]{\textbf{#1}} \)

    \( \newcommand{\vectorD}[1]{\overrightarrow{#1}} \)

    \( \newcommand{\vectorDt}[1]{\overrightarrow{\text{#1}}} \)

    \( \newcommand{\vectE}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{\mathbf {#1}}}} \)

    \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} } \)

    \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash {#1}}} \)

    \(\newcommand{\avec}{\mathbf a}\) \(\newcommand{\bvec}{\mathbf b}\) \(\newcommand{\cvec}{\mathbf c}\) \(\newcommand{\dvec}{\mathbf d}\) \(\newcommand{\dtil}{\widetilde{\mathbf d}}\) \(\newcommand{\evec}{\mathbf e}\) \(\newcommand{\fvec}{\mathbf f}\) \(\newcommand{\nvec}{\mathbf n}\) \(\newcommand{\pvec}{\mathbf p}\) \(\newcommand{\qvec}{\mathbf q}\) \(\newcommand{\svec}{\mathbf s}\) \(\newcommand{\tvec}{\mathbf t}\) \(\newcommand{\uvec}{\mathbf u}\) \(\newcommand{\vvec}{\mathbf v}\) \(\newcommand{\wvec}{\mathbf w}\) \(\newcommand{\xvec}{\mathbf x}\) \(\newcommand{\yvec}{\mathbf y}\) \(\newcommand{\zvec}{\mathbf z}\) \(\newcommand{\rvec}{\mathbf r}\) \(\newcommand{\mvec}{\mathbf m}\) \(\newcommand{\zerovec}{\mathbf 0}\) \(\newcommand{\onevec}{\mathbf 1}\) \(\newcommand{\real}{\mathbb R}\) \(\newcommand{\twovec}[2]{\left[\begin{array}{r}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\ctwovec}[2]{\left[\begin{array}{c}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\threevec}[3]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\cthreevec}[3]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\fourvec}[4]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\cfourvec}[4]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\fivevec}[5]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\cfivevec}[5]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\mattwo}[4]{\left[\begin{array}{rr}#1 \amp #2 \\ #3 \amp #4 \\ \end{array}\right]}\) \(\newcommand{\laspan}[1]{\text{Span}\{#1\}}\) \(\newcommand{\bcal}{\cal B}\) \(\newcommand{\ccal}{\cal C}\) \(\newcommand{\scal}{\cal S}\) \(\newcommand{\wcal}{\cal W}\) \(\newcommand{\ecal}{\cal E}\) \(\newcommand{\coords}[2]{\left\{#1\right\}_{#2}}\) \(\newcommand{\gray}[1]{\color{gray}{#1}}\) \(\newcommand{\lgray}[1]{\color{lightgray}{#1}}\) \(\newcommand{\rank}{\operatorname{rank}}\) \(\newcommand{\row}{\text{Row}}\) \(\newcommand{\col}{\text{Col}}\) \(\renewcommand{\row}{\text{Row}}\) \(\newcommand{\nul}{\text{Nul}}\) \(\newcommand{\var}{\text{Var}}\) \(\newcommand{\corr}{\text{corr}}\) \(\newcommand{\len}[1]{\left|#1\right|}\) \(\newcommand{\bbar}{\overline{\bvec}}\) \(\newcommand{\bhat}{\widehat{\bvec}}\) \(\newcommand{\bperp}{\bvec^\perp}\) \(\newcommand{\xhat}{\widehat{\xvec}}\) \(\newcommand{\vhat}{\widehat{\vvec}}\) \(\newcommand{\uhat}{\widehat{\uvec}}\) \(\newcommand{\what}{\widehat{\wvec}}\) \(\newcommand{\Sighat}{\widehat{\Sigma}}\) \(\newcommand{\lt}{<}\) \(\newcommand{\gt}{>}\) \(\newcommand{\amp}{&}\) \(\definecolor{fillinmathshade}{gray}{0.9}\)

    While the focus of this textbook is on organic reactions occuring in living cells, if you are a chemistry major, or are planning to take a standardized exam such as the MCAT, you will need to be familiar with a number of laboratory synthesis reactions. Here, we review the lab synthesis reactions covered in this text, which include most of the reactions typically covered in traditional organic texts. Click on the chapter/section number for direct links to the section where these reactions are introduced.

    NOTE: content below redirects to an older edition of the text, which differs from the current version in some content and organization.

     

    Section 8.5B:

    image002.png

    alcohols converted into good leaving groups

     

     

    image004.png

    image006.png

     

     

    Section 9.1B:

    image008.png

    Williamson ether synthesis

    alkyl halide must be methyl or primary to avoid competing elimination

     

     

    Section 11.4B:

    image010.png

    cyclic acetal ‘protects’ ketone/aldehyde group – stable to bases/nucleophiles

    deprotect with aqueous acid

     

    Section 12.2D:

     

    image012.png

    activates carboxylic acids

     

    image014.png

    acetic anhydride is a good acetyl group donor (activated acetic acid)

    adds acetyl group to acohols, amines

     

     

    Section 13.6A

    image016.png

    goes through enamine intermediate

     

    image018.png

    haloform reaction – also works with Br2, I2

     

     

    Section 13.6B

    image020.png

    Wittig reaction

     

    Section 13.6C

    image022.png

     

     

    Section 13.6D

    image024.png

    Grignard reagent – carbon nucleophile

    No acidic protons can be present (it’s a strong base)

    Can also use R-Cl

     

    image026.png

     

    image028.png

     

    image030.png

    Grignards add to esters, acid chlorides twice

     

    image032.png

    organolithium – similar to Grignard

     

    image034.png

    Gilman reagent

     

    image036.png

    Gilman reagent will react with alkyl, vinyl halides as well as carbonyls

     

    image038.png

    Gilman reagent will add once to acid chlorides to make a ketone

     

    Section 14.2B

    image040.png

    nucleophilic aromatic substitution

     

    Section 14.3A

    image042.png

    Hoffman elimination - least substituted alkene produced

     

    image044.png

    Cope elimination

     

     

    Section 15.2B

    image046.png

    image048.png

     

    Section 15.2D

    image050.png

    anti-Markovnikov addition of water to alkene. Notice syn addition!

     

    image052.png

     

    image054.png

     

    image056.png

     

    image058.png

    method to protect alcohol – remove with H3O+

     

    image060.png

    another alcohol protecting group: remove with F- ion

     

    Section 15.6A:

    image062.png

    watch out for the possibility of carbocation rearrangements!

     

    image064.png

     

    image066.png

    watch out for the possibility of carbocation rearrangements!

     

    image068.png

     

    image070.png

    ortho-para directing vs. meta-directing groups

    Section 15.7A:

    image072.png

    Markovnikov addition of water without possibility of carbocation shifting

     

    Section 15.7C:

    image074.png

    pinacol rearrangement

    image076.png

    Hoffman rearrangement

     

    Section 15.10:

    image078.png

    Diels-Alder: cis/trans stereoselectivity

     

    image080.png

    bicyclic Diels-Alder product - no stereoselectivity

     

    image082.png

     

    image084.png

    Cope rearrangement

     

    image086.png

    Claisen rearrangement

     

    Section 16.11B:

    image088.png

     

    image090.png

     

    Section 16.13A:

    image092.png

    reduces aldehydes/ketones, but not carboxylic acid derivatives

     

    image094.png

    reduces aldehydes, ketones, carboxylic acid derivatives

     

    image096.png

    can reduce ester/amide to aldehyde (LiAlH4 can't do this)

     

    Section 16.13B:

    image098.png

     

    image100.png

    alkynes, aldehyde, ketones, nitro groups also reduced by H2/Pt (but not acid derivatives!)

     

    image102.png

    alkyne to cis-alkene

     

    image104.png

    alkyne to trans-alkene

     

     

    Section 16.13C:

    image106.png

    image108.png

     

    Section 16.13D:

    image110.png

    primary alcohol to acid

     

    image112.png

    secondary alcohol to ketone

    image114.png

    oxidation at the benzylic position

     

    image116.png

    Swern oxidation

     

    image118.png

    abbreviated PCC

     

    image120.png

    image122.png

     

     

    image124.png

    cis diols cleaved, not trans

     

    image126.png

    image128.png

     

    image130.png

    KMnO4 also oxidizes primary alcohols and aldehydes to acids

    image132.png

     

    Section 17.2B:

    image134.png

    radical halogenation is regiospecific – depends on stablity of radical intermediate

    image136.png

    image138.png

    NBS can be source of Br in radical halogenation reactions

    regiospecificity: benzylic / allylic

    Organic Chemistry With a Biological Emphasis by Tim Soderberg (University of Minnesota, Morris)

    This page titled Appendix II: Review of laboratory synthesis reactions is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by via source content that was edited to the style and standards of the LibreTexts platform.

    This page titled Appendix II: Review of laboratory synthesis reactions is shared under a CC BY-NC-SA 4.0 license and was authored, remixed, and/or curated by Tim Soderberg via source content that was edited to the style and standards of the LibreTexts platform.

    1. Back to top
    • Was this article helpful?

    Recommended articles

    1. Article type
      Chapter
      Author
      Tim Soderberg
      License
      CC BY-NC-SA
      License Version
      4.0
      Show Page TOC
      no on page
    2. Tags
      1. source@https://digitalcommons.morris.umn.edu/chem_facpubs/1/