91Ó°ÊÓ

Beginning with acetylene and any alkyl halide needed, how would you synthesize the following compounds?

(a)Decane

(b)2,2-Dimethylhexane

(c)Hexanal

(d)2-Heptanone

Show how you could prepare the following compounds from 4-methyl-3- penten-2-one, ${\left({\mathbf{CH}}_{\mathbf{3}}\right)}_{\mathbf{2}}\mathbf{C}\mathbf{=}{\mathbf{CHCOCH}}_{\mathbf{3}}$

(a)

(b)

(c)

Question: Show the structures of the fragments you would expect in the mass spectra of the following molecules:

Name the following alkynes, and predict the products of their reaction

With:

(1) ${\mathbf{H}}_{\mathbf{2}}$in the presence of a Lindlar’s catalyst

(2) ${\mathbf{H}}_{\mathbf{3}}{\mathbf{O}}^{\mathbf{+}}$in the presence of ${\mathbf{H}}_{\mathbf{2}}{\mathbf{SO}}_{\mathbf{4}}$

Propose structures for compounds that fit the following mass-spectraldata:

(a) A hydrocarbon with M⁺= 132

(b) A hydrocarbon with M⁺=166

(c) A hydrocarbon with M⁺= 84

Question: Propose structures for compounds that fit the following mass-spectral data:

(a) A hydrocarbon with ${\mathbf{M}}^{\mathbf{+}}\mathbf{=}\mathbf{132}$

(b) A hydrocarbon with ${\mathbf{M}}^{\mathbf{+}}\mathbf{=}\mathbf{166}$

(c) A hydrocarbon with ${\mathbf{M}}^{\mathbf{+}}\mathbf{=}\mathbf{84}$

From what alkyne might each of the following substances have been made? (Green = Cl.)

Write molecular formulas for compounds that show the following molecularions in their high-resolution mass spectra, assuming that C, H, N,and O might be present. The exact atomic masses are: 1.00783(¹H), 12.00000(¹²C) , 14.00307 (¹⁴N) , 15.99491(¹⁶O) .

(a) M+ = 98.0844

(b) M⁺= 123.0320

Question: Write molecular formulas for compounds that show the following molecular ions in their high-resolution mass spectra, assuming that C, H, N, and O might be present. The exact atomic masses are: 1.00783 $\left({}_{}{}^{1}H\right)$, 12.00000 $\left({}_{}{}^{12}C\right)$, 14.00307 $\left({}_{}{}^{14}N\right)$, 15.99491 $\left({}_{}{}^{16}O\right)$.

$$\begin{gathered} \mathbf{a}\mathbf{)}\mathbf{}{\mathbf{M}}^{\mathbf{+}}\mathbf{=}\mathbf{98}\mathbf{.}\mathbf{0844} \\ \mathbf{b}\mathbf{)}\mathbf{}{\mathbf{M}}^{\mathbf{+}}\mathbf{=}\mathbf{123}\mathbf{.}\mathbf{0320} \end{gathered}$$

How would you prepare the following substances, starting from any

compounds having four carbons or fewer?