Question 1

Which of the following is the correct IUPAC name for the alkyne shown below?

$
\begin{array}{c}
	ext{CH}_3-	ext{C}\equiv	ext{C}-	ext{CH}_2-	ext{CH}_2-	ext{CH}_3
\end{array}
$

Accepted Answer

2-Hexyne

Question 2

What is the major product when 2-methyl-2-butene reacts with HBr (no peroxides present)?

$
\begin{array}{c}
	ext{CH}_2=	ext{C}(	ext{CH}_3)-	ext{CH}_2-	ext{CH}_3 + 	ext{HBr} ightarrow ?
\end{array}
$

Accepted Answer

2-Bromo-2-methylbutane

Question 3

Which of the following best describes the hybridization of the carbon atoms numbered 1 and 2 in the molecule below?

$
\begin{array}{c}
	ext{Ph}-	ext{C}\equiv	ext{C}-	ext{CH}_3
\end{array}
$

Accepted Answer

Both are sp hybridized

Question 4

What is the major product of the following reaction?

$
\begin{array}{c}
	ext{Cyclohexene} + 1) 	ext{BH}_3, 	ext{THF} \ 2) 	ext{H}_2	ext{O}_2, 	ext{NaOH} ightarrow ?
\end{array}
$

Accepted Answer

Cyclohexanol

Question 5

Which set of reagents would best convert 1-butyne to 2-butanone?

$
\begin{array}{c}
	ext{CH}_3	ext{C}\equiv	ext{CCH}_2	ext{CH}_3 \xrightarrow{?} 	ext{CH}_3	ext{COCH}_2	ext{CH}_3
\end{array}
$

Accepted Answer

HgSO$_4$, H$_2$SO$_4$, H$_2$O

Question 6

Which of the following compounds would show a strong IR absorption near 3300 cm$^{-1}$ and a sharp absorption near 2100 cm$^{-1}$?

$
\begin{array}{c}
	ext{A) CH}_3	ext{CH}_2	ext{C}\equiv	ext{CH} \ 	ext{B) CH}_3	ext{CH}_2	ext{C}\equiv	ext{CCH}_3 \ 	ext{C) CH}_3	ext{CH}_2	ext{CH}_2	ext{CH}_3 \ 	ext{D) CH}_3	ext{COCH}_3
\end{array}
$

Accepted Answer

A) CH$_3$CH$_2$C$$CH

Question 7

A compound with molecular formula C$_5$H$_{10}$ shows a triplet at $$ 1.0 ppm and a quartet at $$ 2.3 ppm in its $^1$H NMR spectrum. Which structure is most consistent with this data?

Accepted Answer

CH$_3$CH$_2$COCH$_3$

Question 8

Which of the following statements about the reaction of 2-butyne with NaNH$_2$ followed by ethyl bromide is correct?

$
\begin{array}{c}
	ext{CH}_3	ext{C}\equiv	ext{CCH}_3 \xrightarrow{1.\ NaNH_2,\ 2.\ C_2H_5Br} ?
\end{array}
$

Accepted Answer

The product is 3-hexyne

Question 9

Which of the following pairs of compounds can be distinguished by their mass spectra due to the presence of a bromine atom?

Accepted Answer

Bromocyclohexane and cyclohexane

Question 10

Which of the following compounds would give a positive result in the Tollens' test (silver mirror test)?

Accepted Answer

Benzaldehyde

Question 11

Which of the following compounds would show a strong IR absorption at both 2730 cm$^{-1}$ and 2820 cm$^{-1}$?

Accepted Answer

Benzaldehyde

Question 12

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

$
	ext{H}_3	ext{CO}-	ext{CH}_2-	ext{CH}_2-	ext{OCH}_3
$

Accepted Answer

1

Question 13

Which of the following is the correct IUPAC name for the compound below?

$
\begin{array}{c}
	ext{CH}_3-	ext{CH}_2-	ext{C}(	ext{CH}_3)_2-	ext{CH}_2-	ext{CH}_3
\end{array}
$

Accepted Answer

3,3-Dimethylpentane

Question 14

Which of the following best describes the product of the reaction below?

$
\begin{array}{c}
	ext{Cyclohexene} + 	ext{Br}_2, 	ext{CCl}_4 ightarrow ?
\end{array}
$

Accepted Answer

trans-1,2-Dibromocyclohexane

Question 15

Which of the following statements about enantiomers is correct?

Accepted Answer

They have identical physical properties except for the direction in which they rotate plane-polarized light.

Question 16

Which of the following compounds would give a singlet in the $^1$H NMR spectrum for all its protons?

Accepted Answer

Tetramethylsilane (TMS)

Question 17

Which of the following is a correct method to distinguish between 1-butyne and 2-butyne using IR spectroscopy?

Accepted Answer

1-Butyne shows a terminal alkyne C-H stretch near 3300 cm$^{-1}$, while 2-butyne does not.

Organic Chemistry Test 3 Study Guide: Alkenes, Alkynes, Nomenclature, Spectroscopy, and Reaction Mechanisms

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