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Z - Chem 2210 (S&T) > Final, Just Reagents > Flashcards

Final, Just Reagents Flashcards

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1
Q

What would RX produce if combined with Li, Mg, or RONa?

A

RLi (with 2 Li)
ROR (with RONa)
RMgX (with Mg)

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2
Q

What general type of reactions does RX undergo? What are the usual partners?

A

SN1 (weaker nuc)
SN2 (strong nuc)
E2 (strong base)

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3
Q

What reactions do vicinal or geminal dihalides undergo?

A

Two E2 reactions with a strong base to form an alkyne

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4
Q

What reactions do MeX or EtX undergo?

A

Addition to =C: to form -CMe or -CEt

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5
Q

What general type of reaction can 3* alcohols undergo? What will they produce if combined with HX? Include stereochemistry.

A

E1 (strong acid)

Form RX (with HX), SN1 path

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6
Q

What general type of reactions can a 2* alcohol undergo and what kinds of products can it form when combined with HX? Include stereochemistry.

*Reduction questions on another flashcard

A 
E1 (strong acid)
Form RX (with HX), carbocation intermediate
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7
Q

What sort of things will a 2* alcohol be reduced to? What compounds will produce what products?

A

only ketones

Any of:
Na2Cr2O7 then H2SO4/H2O

KMnO4/OH-/heat then H+

PCC

DMSO/ClC(=O)C(=O)Cl then Et3N

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8
Q

What kind of compounds can be produced from a 1* alcohol reacting with a HX? Include stereochemistry.

*Reduction questions on another flashcard

A

Form RX (need HX)

inversion due to SN2

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9
Q

What sort of things will a 1* alcohol be reduced to? What compounds will produce what products?

A

Carboxylic Acids (Na2Cr2O7 then H2SO4/H2O or KMnO4/OH-/heat then H+)

Aldehydes (PCC or DMSO/ClC(=O)C(=O)Cl then Et3N)

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10
Q

What two compounds can be formed by any alcohol other than 3* when combined with PBr3 or SOCl2?

A

RBr (PBr3)

RCl (SOCl2)

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11
Q

How can alcohols be transformed into good intermediates (better leaving groups)?

A

Add TsCl or MsCl to make ROTs or ROMs

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12
Q

What will two identical alcohols and heat/light produce?

A

A symmetric ether

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13
Q

What special kinds of ethers can be formed by alcohols combining with 2-methypropene or ClSi(Me)3 ? What will they combine with?

A

Tert-butyl (RCH2OH, H2SO4 catalyst and 2-methyl-1-propene)

Silyl (all alcohols, base like Et3 or Pyridine, ClSi(Me)3)

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14
Q

What are the three ways an alkene can be turned into an alcohol? What would it need to react with and what preference do those mechanisms have for substitution? Include stereochemistry.

A

H+/H2O, carbocation intermediate

  1. Hg(OAc)2/THF/H2O + 2.NaBH4/OH- -> OH most sub, anti
  2. BH3/THF + 2.H2O2/NaOH -> OH least sub, syn + enantiomers
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15
Q

How can alkenes be transformed into compounds containing at least one X? What would they need to react with (3)? Include stereochemistry.

A

Alkyl Halide (HX), carbocation

Alkane Dihalide (X2 in CCl4), anti may produce enantiomers or meso

Alkane Halohydrin (X2 in H2O), anti with enaniomers

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16
Q

What are the two ways alkenes can be transformed into cis-1,2-diols? What would they need to combine with? Include stereochemistry.

A

Cold/Dilute KMnO4/OH- -> Cis-1,2-diols

OsO4 -> Cis-1,2-diols

either may produce enantiomers, depending on the starting alkene

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17
Q

What 2 sorts of cleavage can alkenes undergo? What would they need to react with? What sort of alkenes would produce what products?

A

+ Ht KMnO4/OH- + H+ -> Carboxylic Acid or Ketone or CO2/H2O by replacing the double bond with =O and replacing any hydrogens with -OH

O3 (then Me2S) -> Aldehyde or Ketone by replacing the double bond with =O

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18
Q

Describe the formation of epoxides from alkenes. Include stereochemistry.

A

The addition of a peracid (including mCPBA) will add an O across the double bond. May produce meso products or enantiomers.

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19
Q

Describe addition reactions of HX to alkynes. Include the effects of multiple equivalents and stereochemistry.

A

+1 HX -> RC(X)=CH
+2 HX -> RC(X)2-CH2R

H on less sub, X on most, anti addition

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20
Q

Describe addition reactions of X2 to alkynes. Include the effects of multiple equivalents and stereochemistry.

A

+1 X2 in CCl4 -> RC(X)=C(X)R
+2 X2 in CCl4 -> RC(X2)-C(X2)R

anti addition

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21
Q

Describe all 3 ways alkynes can be hydrogenated.

A

+ H2 with NiB2(P-2) -> Cis-Alkenes
+ H2 with Pd/CaCO3 (Lindlar)-> Cis-Alkene

+ Li/NH3 or Na/NH3 -> Trans-Alkene

+ H2 with Pd/Ni/Pt/Rh/Ru -> Alkane

22
Q

What special kind of reactions can a terminal C on a triple bond undergo?

A

+ NaNH2 -> ☰C:

23
Q

What special kind of reactions can a terminal CX on a double bond undergo?

A

+ NaNH2 -> ☰C (an E2)

24
Q

What three kinds of reactions rely primarily on an acid? What kinds are used for each?

(hint: one general, one alkene, one epoxide)

A

E1 (strong)
Hydrogenation of Alkenes (dilute)
Opening of epoxides

25
Q

What is Hg(OAc)2/THF/H2O then NaBH4/OH- used for? What kind of sterochemistry is involved?

A

Formation of alcohols from alkenes, anti addition of OH and H, OH most substituted side

26
Q

What is BH3/THF then H2O2/NaOH used for? What kind of stereochemistry is involved?

A

Formation of alcohols from alkenes, syn addition of OH and H, OH least substituted side

27
Q

What sort of things would X2 be used for under normal conditons? (react with alkene or alkyne)

A

React with alkene in CCl4 to form alkane dihalide (anti addition)

React with alkene in H2O to form alkane halohydrin (anti addition)

React with alkyne in CCl4 to form RC(X)=C(X)R (1eq) or RC(X2)-C(X2)R (2eq) (anti addition)

28
Q

What would Br2 plus heat or light be used for?

A

Radical reaction with RH to produce RBr, most substituted products

29
Q

What would Cl2 plus heat or light be used for?

A

Radical reaction with RH to produce RCl, all products

30
Q

What are the three kinds of reactions that involve some form of KMnO4? (1,2 cleavage, oxidation)

A

Cold/Dilute with OH- + alkene = cis-1,2-diols

Hot with OH- and H+ in a second step + alkene = carboxylic acid, ketone, or CO2/H2O

Hot with OH- and H+ in a second step will oxidize 2* alcohol =ketone

Hot with OH- and H+ in a second step will oxidize 1* alcohol =carboxylic acid

31
Q

What sort of things would OsO4 (osmium tetroxide) be used for?

A

formation of cis-1,2-diols from alkene

32
Q

What sort of things would O3 + Me2S in a second step be used for?

A

formation of aldehydes and ketones from alkenes

33
Q

What sort of things would NaNH2 be used for?

A

remove H from terminal alkyne to leave a lone pair

remove X from terminal alkene to form a triple bond

34
Q

Describe the addition reactions of HX (2, alkene and alkyne)

A

To alkenes to form alkyl halides (carbocation intermediate, X on most substituted side)

To alkynes to form RC(X)=CHR, then RC(X)2-CHR (each time is anti addition with X on more substituted)

35
Q

Describe the reactions of HX with various ethers: symmetric, unsymmetric where one side is 3*/benxylic/allylic, unsymmetric ethers (other types)

A

Symmetrical:
ROR + 1 HBr -(heat)-> HOR + RBr
ROR + 2 HBr -(heat)-> 2RBr + H2O

One side is tertiary/benzylic/allylic -> that side will grab the X in an SN1, if not it will go via SN2 (X the least substituted carbon on the opposite side, produce alcohol and inverted alkyl halide)

36
Q

Describe the use of HBr in radical reactions with RCH=CH2. Include preferred conditions.

A

High temperatures and low concentrations.

Form RCH2CH2Br

37
Q

What sort of things would NBS be used for? What would it be paired with (2)?

A

Production of Bromine Radials and Br2
(RCH=CH2)

Allyic Bromination of Alkenes with heat/light and ROOR
(+ RCH=CHCH3 -> RCH=CHCH2Br)

38
Q

What sort of things would ROOR be used for? What might it be paired with?

A

Prompt Anti-Markovnikov reactions
Low concentrations of HBr, Heat

Promt Radical Reactions
NBS, HBr

39
Q

What sort of things would PBr3 be used for?

A

Combine with alcohols (all except 3*) to replace OH with Br

40
Q

What sort of things would SOCl2 be used for?

A

Combine with alcohols (all except 3*) to replace OH with Cl

41
Q

What sort of things would TsCl or MsCl be used for?

A

React with alcohols to convert OH into a good leaving group (OTs or OMs)

42
Q

What sort of things would ClSi(Me)3 be used for?

A

Formation of silyl ethers with alsohols and a base like Et3N or pyridine

43
Q

Give some examples of peracids and describe what they are used for.

A

-CO3H or mCPBA are used for the formation of epoxides from alkenes

44
Q

Describe the various types of ring opening an epoxide can undergo (3).

A

Ring opening with nucleophile, end up with base on less substituted side and OH on more, both anti

Ring opening with acid, end up with conjugate base on more substituted side and OH on least, both anti

Ring opening with grignard reagent (RMgX), end up with R on less substituted and OH on more, anti

45
Q

What is NaBH4 (type of compound)? What will it produce when reacting with aldehydes or ketones?

A

Weak reducing agent

Reduce aldehydes to primary or methyl alcohols

Reduce ketones to secondary alcohols

46
Q

What is LiAlH4 (type of compound)? What will it produce when reacting with aldehydes, ketones, carboxylic acids, esters, and alkyl halides?

A

Strong reducing agent

Reduce aldehydes to primary or methyl alcohols

Reduce ketones to secondary alcohols

Reduce carboxylic acids to primary alcohols (replace =O with two -H)

Reduce esters to alcohols (break bond from O to O, add H to each)

Reduce alkyl halides to alkanes (RH)

47
Q

What sort of things would Na2Cr2O7 then H2SO4/H2O be used for (2)? (oxidizing agent)

A

Oxidize 1* alcohols to carboxylic acids

Oxidize 2* alcohols to ketones

48
Q

What sort of things would PCC be used for (2)? (oxidizing agent)

A

Oxidize 1* alcohols to aldehydes

Oxidize 2* alcohols to ketones

49
Q

What sort of things would DMSO/ClC(=O)C(=O)Cl then Et3N be used for (2)? What is this called? (oxidizing agent)

A

Oxidize 1* alcohols to aldehydes

Oxidize 2* alcohols to ketones

Swern oxidation

50
Q

Describe RLi. What kind of reactions will it undergo (3)? (Terminal alkyne, water, synthesis)

A

Alkyl Lithium, an organometallic compound, R- and Li+

Remove terminal hydrogen from alkyne, leaving lone pairs

Produce RH from H2O (similar mechanism also applies to alcohols)

Synthesize deuterated/tritiated compounds when added to D2O or T2O

51
Q

Describe RMgX, including its name. What kinds of reactions will it undergo (3)? (ignore production of alcohols, include alkyne, water, and epoxides)

A

Remove terminal hydrogen from alkyne, leaving lone pairs

Produce RH from H2O (similar mechanism also applies to alcohols)

Ring opening of epoxides, produce R on less substituted and OH on more, anti

52
Q

Describe the four ways RMgX can produce alcohols. (hint: two main categories, ketone like or ester)

A

Break =O by adding -R to C and then add H to O- (will turn formaldehyde into primary alcohols, aldehydes into secondary alcohols, and ketones into tertiary alcohols)

Turn the =O from an ester into -OH, replace OR with two R groups from RMgX, (ester to tertiary alcohol)

Z - Chem 2210 (S&T) (14 decks)

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