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Exam 10: Determining the Structure of Organic Compounds

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Question 41

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Which statements are true about the mass spectrum of 1-bromobutane?

A) Peaks of approximately equal intensity are observed at m/z 136 and 138 .
B) The major fragmentation occurs by cleavage of the C-Br bond.
C) The most intense peak occurs at m/z 43 .
D) both A and B
E) both B and C

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Question 42

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Which of the following $\mathrm { C } - \mathrm { H }$ bonds shows IR absorption at the lowest wavenumber? I. II. III. $\mathrm { C } - \mathrm { C } - \mathrm { H }$ IV. $\mathrm { C } = \mathrm { C } - \mathrm { H }$ V. $\mathrm { C } \equiv \mathrm { C } - \mathrm { H }$

A) I
B) II
C) III
D) IV
E) V

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Question 43

Multiple Choice

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What hydrogens give the ¹H NMR signal with the lowest frequency?

How many signals would you expect to see in the ¹H NMR spectrum of the following compound?

1H nuclei located near electronegative atoms tend to be ________ relative to ¹H nuclei that are not.

Identify the compound. $\mathrm { C } _ { 5 } \mathrm { H } _ { 8 } \mathrm { O } : 3000,1750 \mathrm {~cm} ^ { - 1 }$

Identify the compound: $\mathrm { C } _ { 5 } \mathrm { H } _ { 10 } \mathrm { O } _ { 2 }$ IR $\left( \mathrm { cm } ^ { - 1 } \right)$ : $\quad 3300 - 2800 ($ v. broad), 2950, 1710 13C NMR (8): 220 (s), 45 (s), 12 (q)

What hydrogens give the ¹H NMR signal with the lowest frequency? $\mathrm { F } - \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { Br }$ $\begin{array} { l l l l l } \quad\quad1 & 2 & 3 & 4 & 5 \end{array}$

Which compound has an absorption band at 3300 cm^-1?

What region of the electromagnetic spectrum has the greatest energy per photon?

Identify the compound: $\begin{aligned}\mathrm { C } _ { 5 } \mathrm { H } _ { 8 } \mathrm { O } _ { 4 } : & \mathrm { IR } \left( \mathrm { cm } ^ { - 1 } \text { ) : } 2800 - 3300 \text { (broad) , 2950, } 1740 \right. \\&{}^{ 13} \mathrm { C } \text { NMR: } 17.3 \mathrm { ppm } \text { (q) , } 44.3 \mathrm { ppm } \text { (s) , } 210.5 \mathrm { ppm } \text { (s) }\end{aligned}$

Identify the compound, with molecular formula C₄H₁₀O, that gives the following 1H NMR data: Triplet at 1.13 ppm Quartet at 3.38 ppm What is the structure of the compound?

A compound gave a signal at 203 ppm in its ${}^{13 }\mathrm { C } \mathrm { NMR }$ spectrum. How would it be possible to tell if the compound is an aldehyde or a ketone in a proton-coupled ${}^{13} \mathrm { C } \text { NMR }$ pectrum?

Identify the compound: $\begin{array} { l l } \mathrm { C } _ { 6 } \mathrm { H } _ { 10 } & \\\text { IR } ( \mathrm { cm } - 1 ) : & 2950,2230 \\\text { 1H NMR (d): } & 2.0 ( 1 \mathrm { H } , \text { septet), } 1.8 ( 3 \mathrm { H } , \mathrm { s } ) , 0.9 ( 6 \mathrm { H } , \mathrm { d } ) \\\text { 13C NMR (d): } & 78 ( \mathrm {~s} ) , 72 ( \mathrm {~s} ) , 45 ( \mathrm {~d} ) , 18 ( \mathrm { q } ) , 15 ( \mathrm { q } )\end{array}$

What hydrogens give the ¹H NMR signal with the highest frequency? $\left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { CH } - \mathrm { O } - \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 3 }$ $\begin{array} { l l l l l }\quad 1 & \quad2 &\quad 3 &\quad 4 & 5 \end{array}$

How many signals are in the ¹³C NMR spectrum of the following compound?

Which statement explains the information we can gain from infrared spectroscopy?

Which region of the electromagnetic spectrum, IR or X-ray, has light waves of lower frequency?

Which of the following compounds has the greatest λ_max ?

Identify the compound: $\mathrm { C } _ { 7 } \mathrm { H } _ { 12 } : \text { IR } \left( \mathrm { cm } ^ { - 1 } \right) : 3300,2950,2220 ; {}^{13} \mathrm { C } \text { NMR: } 5 \text { signals }$