Question 1

Which of the following reagents would most likely result in an E2 elimination when reacted with 2-bromopropane?

Accepted Answer

$$\mathrm{NaOEt} / $$ethanol$

Question 2

What is the major product when cyclohexanol is treated with $$\mathrm{H_2SO_4}$$ and heat?

Accepted Answer

Cyclohexene

Question 3

Which of the following best describes the stereochemistry of the product formed when (Z)-2-butene reacts with $$\mathrm{Br_2$} in$$ $$\mathrm{H_2O}$$?

Accepted Answer

Anti addition, leading to enantiomers

Question 4

A student treats 1-hexene with $$\mathrm{1. BH_3$, 2. H_2O_2, OH^-}$$ and obtains an alcohol. What is the regiochemistry of the product?

Accepted Answer

Anti-Markovnikov addition at the terminal carbon

Question 5

Which of the following molecules would show 5 distinct $$^1\mathrm{H}$$ NMR signals?

Accepted Answer

$$\mathrm{CH_3CH_2CH_2CH_2OH} (1-$$butanol)

Question 6

In the $$^1\mathrm{H}$$ NMR spectrum of para-xylene ($$\mathrm{C_6H_4(CH_3$)_2}$$), which protons will have the highest chemical shift (downfield)?

Accepted Answer

Aromatic ring protons

Question 7

A compound with molecular formula $$\mathrm{C_4H_8O_2}$$ shows IR absorptions at 3350 cm$$^{-1}$$ and 1738 cm$$^{-1}. $$Which functional groups are present?

Accepted Answer

Alcohol and ester

Question 8

Which splitting pattern would you expect for the bolded protons in $$\mathrm{CH_3CH_2OH} ($$ethanol) in $$^1\mathrm{H}$$ NMR?

Accepted Answer

Triplet for $$\mathrm{CH_3$}$$, quartet for $$\mathrm{CH_2$}$$

Question 9

Which of the following reactions will result in syn dihydroxylation of an alkene?

Accepted Answer

$$\mathrm{$$OsO_4$$}$$, $$\mathrm{H_2O_2}$$

Question 10

A student performs ozonolysis on cyclohexene. What is the major organic product after reductive workup with $$\mathrm{Me_2S}$$?

Accepted Answer

Adipaldehyde ($$\mathrm{OHC(CH_2$)_4CHO})$$

Question 11

Which of the following best explains why $$\mathrm{E2}$$ eliminations are favored with strong, bulky bases?

Accepted Answer

Bulky bases hinder substitution, favoring elimination

Question 12

What is the expected product when 1-hexene is treated with $$\mathrm{Br_2$} in$$ $$\mathrm{H_2O}$$?

Accepted Answer

2-bromo-3-hexanol

Question 13

Which of the following statements about $$\mathrm{^1H}$$ NMR chemical shifts is correct?

Accepted Answer

Protons attached to electronegative atoms appear downfield

Question 14

A student observes a quartet at 4.1 ppm and a triplet at 1.2 ppm in the $$^1\mathrm{H}$$ NMR spectrum of an unknown compound. Which compound is most likely present?

Accepted Answer

Ethyl acetate ($$\mathrm{CH_3COOCH_2CH_3})$$

Question 15

Which of the following mechanisms best describes the reaction of 2-bromopropane with $$\mathrm{KOH} in $$ethanol?

Accepted Answer

E2 elimination

Question 16

Which of the following is the correct order of increasing chemical shift (upfield to downfield) in $$^1\mathrm{H}$$ NMR for the following protons: methyl, aromatic, aldehydic?

Accepted Answer

Methyl \u003c Aromatic \u003c Aldehydic

Question 17

Which of the following best describes the product of hydroboration-oxidation of 1-methylcyclopentene?

Accepted Answer

Trans-2-methylcyclopentanol

Question 18

A student performs an SN2 reaction on (S)-2-bromobutane with $$\mathrm{NaOH}. $$What is the stereochemistry of the product?

Accepted Answer

R-2-butanol

Question 19

Which of the following statements about ozonolysis is correct?

Accepted Answer

Ozonolysis cleaves double bonds to form carbonyl compounds

Organic Chemistry Exam 3 Study Guide: Reaction Mechanisms, Alkene Additions, and NMR Spectroscopy

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