Organic Chemistry 2 Test 1 – Flashcards

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question
What is the pKa of HCl?
answer
-8
question
What is the pKa of H3O+?
answer
-2
question
What is the pKa of NH4+?
answer
+9
question
What is the pKa of NH3?
answer
+35
question
What is the pKa of H2O?
answer
+16
question

What is the pKa of -*ROH?

 

 

 

*Note: "R" is a generic representation for various alkyl groups. The bulk of the alkyl group can impact acidity, but for a ballpark pKa value, this works.

answer
+16
question
What is the pKa of -RCOOH?
answer
+5
question
What is the pKa of phenol?
answer
+10
question
What is the pKa of p-toluene sulfonic acid?
answer
-3
question
What is the pKa of -RCOCH2COR-?
answer
+10
question
What is the pKa of -RCOCH3?
answer
+20
question
What is the pKa of HCCH?
answer
+25
question
What is the pKa of H2CCH2?
answer
+44
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What is the pKa of CH4?
answer
+50
question
If you have nitrobenzene, which reaction would you use to make aniline?
answer

Use Zn(Hg) and HCl or

Fe and HCl or

Ni and H2 or

Sn and HCl

question
If you have aniline, which reaction would you use to make nitrobenzene?
answer
CF3COOH
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If you have a COR- group on a benzene ring, how do you make that group into CH2R-?
answer

Zn(Hg) and HCl or

NH2NH2 and OH-

question
If you have a CH2R group on a benzene ring, how do you make that group into COR-?
answer
CrO3, H2SO4, H2O and heat
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If you have SO3H on a benzene ring, how do you get benzene?
answer
H2O, cat. H2SO4 and heat
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If you have aniline, how do you make the NH2 group into HNCOCH3?
answer
H3CCOCl and pyridine
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How do you remove the -COCH3 group from -NH on a benzene ring to get aniline?
answer
NaOH and H2O
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How do you make a OCOCH3 group on a benzene ring starting from phenol?
answer
H3CCOCl and pyridine
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How do you remove a H3CCOO group from a benzene ring to get phenol?
answer
NaOH and H2O
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How do you get anisole from phenol?
answer
NaOH and CH3I
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How do you get phenol from anisole?
answer
With concentrated HI
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How do you prepare an acid chloride (-RCOCl) from a carboxylic acid (-RCOOH)?
answer
With SOCl2
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Describe the halogens (I, Br, Cl, F) in terms of activating/deactivating, EWG/EDG, and directing effects.
answer
The halogens are weak deactivators, weak EWGs, and o and p directors.
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Describe carbonyl groups (-C=OR) in terms of activating/deactivating, EWG/EDG, and directing effects.
answer
The carbonyl groups are moderate deactivators, moderate EWGs, and meta directors.
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Describe -CN, -SO3H, -NH3, -NH2R, -NHR2, -NR3, -CF3, -OH2, and -NO2 in terms of activating/deactivating, EWG/EDG, and directing effects.
answer
These are all strong deactivators, strong EWGs, and meta directors.
question
Describe -NH2, -NHR, -NR2, -OH, and -OR in terms of activating/deactivating, EWG/EDG, and directing effects.
answer
These are all strong activators, strong EDGs, and o and p directors.
question
Describe alkyl, phenyl, and vinyl groups in terms of activating/deactivating, EWG/EDG, and directing effects.
answer
These are all weak activators, weak EDGs, and o and p directors.
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Describe -NHCOR and -OCOR in terms of activating/deactivating, EWG/EDG, and directing effects.
answer
These are moderate activators, moderate EDGs, and o and p directors.
question
What is the Lindlar catalyst and what does it do?
answer

Pd-CaCO3, Pb(OAc)2, and quinoline

 

 It hydrogenates alkynes to cis alkenes.

question
How do you hydrogenate an alkyne to a trans alkene?
answer
Use sodium metal (Na0) and liquid ammonia (NH3(l)).
question
What are the reagents involved in mercury ion catalyzed hydration of an alkyne?
answer
H2SO4, H2O, and HgSO4
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In mercury ion catalyzed hydration of alkynes, does the H2O add to the alkyne according to Markovnikov's rule?
answer
Yes. The O adds to the most highly substituted C.
question
Which reagents are used in anti-Markovnikov hydration of alkynes?
answer

1) BHR2

2) H2O2 and OH-

question
What do we use NBS for?
answer
Adding a single Br to an alkene, as opposed to creating a viinal dihalide, as occurs with excess Br. NBS keeps the concentration of Br very low. Br will add wherever a radical can form (on allyic Hs).
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Do organolithium reagents (R-Li) add 1,2, 1,4, or both to enones?
answer
1,2
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Does LiAlH4 add 1,2, 1,4, or both to enones?
answer
1,2
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Does NaBH4 add 1,2, 1,4, or both to enones?
answer
1,2
question
Do grignard reagents (RMgX) add 1,2, 1,4, or both to enones?
answer
both 1,2 and 1,4
question
Name 3 methods for forming an enone.
answer

1) Aldol condensation

2) Mono alpha-halogenate (acidic conditions), followed up by basic E2 H-X elimination

3) Oxidation of an allylic alcohol using MnO2

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Do organo cuprates (R2CuLi) add 1,2, 1,4, or both to enones?
answer
1,4
question
Does RMgBr + copper salts add 1,2, 1,4, or both to enones?
answer
1,4
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Do enolates add 1,2, 1,4, or both to enones?
answer
1,4 (net)
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Does hydroxide (OH-) add 1,2, 1,4, or both to enones?
answer
1,4 (net)
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Do alkoxides (OR-) add 1,2, 1,4, or both to enones?
answer
1,4 (net)
question
Do amines add 1,2, 1,4, or both to enones?
answer
1,4 (net)
question
What do you get when you add H3PO2 to an arenediazonium ion?
answer
Benzene
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What do you get when you add H2O to an arenediazonium ion?
answer
Phenol
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What do you get when you add CuBr to an arenediazonium ion?
answer
Bromobenzene
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What do you get when you add CuCl to an arenediazonium ion?
answer
Chlorobenzene
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What do you get when you add CuCN to an arenediazonium ion?
answer
A nitrile group on a benzene ring (C triple bond N substituent)
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What do you get when you add HBF4 to an arenediazonium ion?
answer
Fluorobenzene
question
What do you get when you add KI to an arenediazonium ion?
answer
Iodobenzene
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