Question 1

Which of the following is the correct product when benzyl alcohol ($$\mathrm{C_6H_5CH_2OH}) is $$treated with sodium hydroxide ($$\mathrm{NaOH}$$)?

Accepted Answer

Sodium phenoxide + water

Question 2

Given the reaction: $$\mathrm{CH_3CH_2CH_2CH_2OH}$$ with $$\mathrm{NaBr}$$ and $$\mathrm{H_2SO_4}$$, what is the major product?

Accepted Answer

$$\mathrm{CH_3CH_2CH_2CH_2Br}$$

Question 3

Which reagent is required to reduce a carboxylic acid ($$\mathrm{RCOOH}) to a $$primary alcohol ($$\mathrm{RCH_2OH}$$)?

Accepted Answer

$$\mathrm{$$LiAlH_4$$}$$, then $$\mathrm{H_2O}$$

Question 4

What is the product of the following reaction: $$\mathrm{CH_3CH_2CH_2CH_2OH}$$ with $$\mathrm{$$PCl_5$$}$$?

Accepted Answer

$$\mathrm{CH_3CH_2CH_2CH_2Cl}$$

Question 5

Which of the following is the correct sequence of reagents to convert a ketone to a secondary alcohol?

Accepted Answer

$$\mathrm{$$NaBH_4$$}$$, then $$\mathrm{H_2O}$$

Question 6

A Grignard reagent ($$\mathrm{CH_3CH_2MgBr}) $$reacts with benzaldehyde ($$\mathrm{C_6H_5CHO}) $$followed by acid workup. What is the product?

Accepted Answer

$$\mathrm{C_6H_5CH(OH)CH_2CH_3}$$

Question 7

What is the major product when 1-bromopropane reacts with aqueous $$\mathrm{NaOH}$$?

Accepted Answer

1-propanol

Question 8

Which of the following is the correct IUPAC name for the compound $$\mathrm{C_6H_4($$OCH_3$$)_2}$$ with methoxy groups at positions 1 and 4?

Accepted Answer

1,4-dimethoxybenzene

Question 9

Which of the following reagents would you use to convert cyclohexene to cyclohexane?

Accepted Answer

$$\mathrm{H_2$}$$, Pd/C

Question 10

In the reaction of tert-butyl alcohol ($$\mathrm{(CH_3$)_3COH}) $$with $$\mathrm{HBr}$$, what is the major organic product?

Accepted Answer

tert-butyl bromide

Question 11

Which of the following is the correct product when cyclohexene is treated with $$\mathrm{mCPBA}$$?

Accepted Answer

Cyclohexene oxide

Question 12

What is the major product when benzonitrile ($$\mathrm{C_6H_5CN}) is $$hydrolyzed under acidic conditions?

Accepted Answer

Benzoic acid ($$\mathrm{C_6H_5COOH})$$

Question 13

Which of the following is the correct product when 1-butanol is oxidized with $$\mathrm{Na_2Cr_2O_7}$$ and $$\mathrm{H_2SO_4}$$?

Accepted Answer

Butanoic acid

Question 14

Which of the following is the correct product when ethylmagnesium bromide ($$\mathrm{C_2H_5MgBr}) $$reacts with acetone ($$\mathrm{CH_3COCH_3}) $$followed by acid workup?

Accepted Answer

$$\mathrm{(CH_3$)_2C(OH)C_2H_5}$$

Question 15

Which of the following is the correct product when 1,4-dimethoxybenzene is treated with $$\mathrm{HBr}$$?

Accepted Answer

1,4-dimethoxybenzene

Question 16

Which of the following is the correct product when cyclohexanol is treated with $$\mathrm{$$POCl_3$$}$$ and pyridine at $$0^\circC$$?

Accepted Answer

Cyclohexene

Question 17

Which of the following is the correct product when 1-butanol is treated with $$\mathrm{HCl}$$ and $$\mathrm{$$ZnCl_2$$}$$?

Accepted Answer

1-chlorobutane

Question 18

Which of the following is the correct product when cyclohexene is treated with $$\mathrm{Br_2$} in$$ $$\mathrm{$$CCl_4$$}$$?

Accepted Answer

trans-1,2-dibromocyclohexane

Question 19

Which of the following is the correct product when 1-butanol is treated with $$\mathrm{H_2SO_4}$$ and heat?

Accepted Answer

1-butene

Organic Chemistry Reaction Mechanisms and Synthesis: Study Notes

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