6.7: In-Text References
- Page ID
- 354432
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\(\newcommand{\avec}{\mathbf a}\) \(\newcommand{\bvec}{\mathbf b}\) \(\newcommand{\cvec}{\mathbf c}\) \(\newcommand{\dvec}{\mathbf d}\) \(\newcommand{\dtil}{\widetilde{\mathbf d}}\) \(\newcommand{\evec}{\mathbf e}\) \(\newcommand{\fvec}{\mathbf f}\) \(\newcommand{\nvec}{\mathbf n}\) \(\newcommand{\pvec}{\mathbf p}\) \(\newcommand{\qvec}{\mathbf q}\) \(\newcommand{\svec}{\mathbf s}\) \(\newcommand{\tvec}{\mathbf t}\) \(\newcommand{\uvec}{\mathbf u}\) \(\newcommand{\vvec}{\mathbf v}\) \(\newcommand{\wvec}{\mathbf w}\) \(\newcommand{\xvec}{\mathbf x}\) \(\newcommand{\yvec}{\mathbf y}\) \(\newcommand{\zvec}{\mathbf z}\) \(\newcommand{\rvec}{\mathbf r}\) \(\newcommand{\mvec}{\mathbf m}\) \(\newcommand{\zerovec}{\mathbf 0}\) \(\newcommand{\onevec}{\mathbf 1}\) \(\newcommand{\real}{\mathbb R}\) \(\newcommand{\twovec}[2]{\left[\begin{array}{r}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\ctwovec}[2]{\left[\begin{array}{c}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\threevec}[3]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\cthreevec}[3]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\fourvec}[4]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\cfourvec}[4]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\fivevec}[5]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\cfivevec}[5]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\mattwo}[4]{\left[\begin{array}{rr}#1 \amp #2 \\ #3 \amp #4 \\ \end{array}\right]}\) \(\newcommand{\laspan}[1]{\text{Span}\{#1\}}\) \(\newcommand{\bcal}{\cal B}\) \(\newcommand{\ccal}{\cal C}\) \(\newcommand{\scal}{\cal S}\) \(\newcommand{\wcal}{\cal W}\) \(\newcommand{\ecal}{\cal E}\) \(\newcommand{\coords}[2]{\left\{#1\right\}_{#2}}\) \(\newcommand{\gray}[1]{\color{gray}{#1}}\) \(\newcommand{\lgray}[1]{\color{lightgray}{#1}}\) \(\newcommand{\rank}{\operatorname{rank}}\) \(\newcommand{\row}{\text{Row}}\) \(\newcommand{\col}{\text{Col}}\) \(\renewcommand{\row}{\text{Row}}\) \(\newcommand{\nul}{\text{Nul}}\) \(\newcommand{\var}{\text{Var}}\) \(\newcommand{\corr}{\text{corr}}\) \(\newcommand{\len}[1]{\left|#1\right|}\) \(\newcommand{\bbar}{\overline{\bvec}}\) \(\newcommand{\bhat}{\widehat{\bvec}}\) \(\newcommand{\bperp}{\bvec^\perp}\) \(\newcommand{\xhat}{\widehat{\xvec}}\) \(\newcommand{\vhat}{\widehat{\vvec}}\) \(\newcommand{\uhat}{\widehat{\uvec}}\) \(\newcommand{\what}{\widehat{\wvec}}\) \(\newcommand{\Sighat}{\widehat{\Sigma}}\) \(\newcommand{\lt}{<}\) \(\newcommand{\gt}{>}\) \(\newcommand{\amp}{&}\) \(\definecolor{fillinmathshade}{gray}{0.9}\)- \(\mathrm{NaH}\) is synthesized by the reaction of sodium with hydrogen—a redox reaction. It is an ionic compound consisting of \(\mathrm{Na}^{+}\) and \(\mathrm{H}^{-}\) (hydride) ions; hydride cannot be produced by deprotonating \(\mathrm{NaH}_{2}\). ↵
- The \(\mathrm{pK}_{a}\) of \(\mathrm{NaH}_{3}\) (the conjugate acid of \(\mathrm{NaH}_{2} {}^{-}\)) is \(33\) ↵
- To use the oxidation number method, we must remember that \(\mathrm{H}\) is less electronegative than \(\mathrm{C}\); so in \(\mathrm{CH}_{4}\), the ON ofcarbon is –4 and each \(\mathrm{H}\) is +1. (This is confusing since we usually consider \(\mathrm{C-H}\) bonds as non-polar). In \(\mathrm{CO}_{2}\), each \(\mathrm{O}\) is –2 and the \(\mathrm{C}\) is +4. Therefore, in \(\mathrm{CO}_{2}\) the carbon is in a higher oxidation state than in CH4↵
- For more information about green chemistry see: https://www.epa.gov/greenchemistry ↵
- It is not necessary here to provide a long list of such reagents since many of them are complex, but it is important to know that there are alternatives should you ever need to oxidize an alcohol. ↵
- The formation of the analogous peroxide \(\mathrm{O-O}\) bond (Bond Dissociation Energy \(140 \mathrm{~kJ} / \mathrm{mol}\)) is even less likely, this bond is even weaker than \(\mathrm{S-S}\) (BDE \(230 \mathrm{~kJ} / \mathrm{mol}\)). ↵
- \(\mathrm{NaBH}_{4}\) and \(\mathrm{LiAlH}_{4}\) both contain a group III element (\(\mathrm{B}, \(\mathrm{Al}\)) here found in the form of the Lewis acid-base complex \(\mathrm{BH}_{4}\) or \(\mathrm{AlH}_{4}\). They are sources of Hydride ion, as shown above. \(\mathrm{LiAlH}_{4}\) is more reactive than \(\mathrm{NaBH}_{4}\). ↵
- Victor Grignard won a Nobel prize for this discovery: https://en.Wikipedia.org/wiki/Victor_Grignard. ↵
- The reaction mechanism is a little more complex than this—actually occurring via one electron transfer—but the result is the same. ↵