Question 1

Refer to the molecule shown in $$image_1. $$Which sequence correctly ranks the protons labeled 1, 2, and 3 in order of increasing acidity?

Accepted Answer

3 \u003c 2 \u003c 1

Question 2

Examine the two Newman projections shown in $$image_2. $$Which statement best describes their relationship?

Accepted Answer

They are different conformations of the same molecule.

Question 3

The Newman projection in $$image_3$$ represents pentane in which conformation?

Accepted Answer

Anti

Question 4

Rank the free radicals I-III shown in $$image_4 in $$order of decreasing stability (most stable to least stable).

Accepted Answer

I \u003e III \u003e II

Question 5

How many asymmetric carbon atoms are present in the compound shown in $$image_5$$?

Accepted Answer

2

Question 6

Which of the following structures in $$image_6$$ corresponds to the correct stereochemical configuration of D-Threonine (2R, 3S)?

Accepted Answer

IV

Question 7

What is the IUPAC name of the compound shown in $$image_7$$?

Accepted Answer

(1R,3S)-1,3-dichloro-1-ethyl-3-methylcyclopentane

Question 8

How many distinct alkene products are possible, including stereoisomers, when the alkyl iodide shown in $$image_8$$ undergoes E2 elimination?

Accepted Answer

4

Question 9

Which of the following compounds shown in $$image_9 is $$not a constitutional isomer of a compound with empirical formula $$\mathrm{C_3H_7O}$$ and formula mass 118.164?

Accepted Answer

Compound 4

Question 10

Which of the following is the best reaction sequence to use if one wants to accomplish a Markovnikov addition of water to an alkene with minimal skeletal rearrangement?

Accepted Answer

oxymercuration-demercuration

Question 11

What is the major product of the reaction shown in $$image_10$$ when treated with NaOCH3 in CH3OH?

Accepted Answer

A cyclohexene with a double bond between the two methyl groups

Question 12

Which of the following best describes the geometry about the carbon-carbon double bond in the alkene shown in $$image_11$$?

Accepted Answer

E

Question 13

Which of the following substrates shown in $$image_12$$ will NOT form a Grignard reagent when treated with Mg/diethylether?

Accepted Answer

Compound 3

Question 14

Which of the following alkyl halides reacts most rapidly via an SN2 reaction with NaCN?

Accepted Answer

1-iodohexane

Question 15

Which of the following alkyl bromides undergoes solvolysis (SN1) in aqueous methanol most rapidly?

Accepted Answer

PhCHBrCH3

Question 16

When an aldehyde is treated with $$\mathrm{$$LiAlH_4$$}$$ followed by addition of $$\mathrm{H_2O}$$, what general class of product results?

Accepted Answer

primary alcohol

Question 17

Which of the following reagents is the best choice for oxidizing a primary alcohol to an aldehyde?

Accepted Answer

pyridinium chlorochromate

Question 18

Which of the following terms best describes the reactive nature of a Grignard reagent?

Accepted Answer

nucleophile

Question 19

What intermolecular forces are present among molecules in dimethyl ether, $$\mathrm{CH_3OCH_3}$$?

Accepted Answer

both London dispersion forces and dipole-dipole forces

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