Chapter 16 Flashcards
What is Formaldehyde?
H-(C=O)-H
What is Acetaldehyde?
H3C-(C=O)-H
What is Acetone?
H3C-(C=O)-CH3
What is Acetophenone?
Ph-(C=O)-CH3
What is Benzophenone?
Ph-(C=O)-Ph
What is Benzaldehyde?
Ph-(C=O)-H
What is an Alkanoyl Group? (also called an acyl group)
-(C=O)-R
What are the two suffixes commonly used aldehyde nomenclature? (one short and one long)
-al (to replace an -e suffix) and (parent chain name)-aldehyde
What is the suffix if a -CHO (aldehyde group) is attached to a ring?
-carbaldehyde
How are dialdehydes named?
omit location number (aldehydes are assumed to be on the ends of the compound) and change the ending to -dial
What is the suffix for ketones?
-one (to replace an -e suffix)
What is the structure for the common names of ketones?
alkyl alkyl ketone
How are diketones named?
both carbonyls require a location number and change the suffix to Dione
if in.a ring, the -e suffix remains and is immediately before the Dione suffix
How are compounds containing both an aldehyde and a ketone named?
compound is named as an aldehyde and the ketone is named as an oxo substituent
ketone needs location number, aldehyde does not
How are aldehydes and ketones named when there is an OH in the same compound?
the OH is a hydroxy substituent
How are cyanohydrins C(-OH)(≣N) produced?
Add NaCN to an aldehyde or a ketone. The =O is replaced with a -OH and -C(triple bond)N
What is the effect of the addition of HCl, H2O, and heat to a cyanohydrin C(-OH)(≣N)?
Produces a carboxylic acid with a double bond on the more substituted side
What is the effect of the addition of LiAlH4 and H2O to a cyanohydrin C(-OH)(≣N)?
Replaces -C(triple bond)N with -CNH2, two hydrogens. (adds four hydrogens total)
What is the effect of the addition of R-PPh3 to an aldehyde or a ketone? Bonus: What is this reaction called?
Replace =O with R
Witting Reaction, The Addition of Ylides/Zwitter ions
What is the effect of adding a primary amine to an aldehyde or ketone? Bonus: What is the product called?
Replace =O with =NR, Imine
What is the effect of adding a secondary amine to an aldehyde or ketone? Bonus: What is the product called?
Replace =O with -NR2 and double bond on more substituted side, Enamine
What is the effect of the addition of N2H4/Oh/heat to an aldehyde or ketone? Bonus: What is this reaction called?
Replace =O with hydrogens, Wolff-Kishner Reduction
What is the effect of the addition of alcohols to aldehydes or ketones? Bonus: What is the product called?
Replace =O with two -OR, acetal
Note: Also produces an intermediate of a hemiacetal, where one of the -OR groups is an -OH
What is the effect of the addition of dialcohols to aldehydes or ketones?
Replace =O with two single bonds to the ends of an ORO (one bond to each O, produces a cyclic compound)
What is the effect of the addition of Ag(NH3)2 to an aldehyde? Bonus: What is this reaction called?
Replaces hydrogen with a single bond to a O-, produces free Ag
Tollen’s Test, Silver Mirror
What is the effect of addition SOCl2 to alcohols?
Forms alkyl chlorides with all alcohol except for 3* (replaces OH with Cl)
What is the effect of the addition of Zn/Hg/HCl to an aldehyde or ketone? Bonus: What is this reaction called?
Replace =O with hydrogens, Clemmensen reduction
What is the effect of the addition of EtSH to an aldehyde or ketone? Bonus: What is the product called?
Replaces =O with two -SEt, thioacetal
What is the effect of the addition of HS-R-SH to an aldehyde or ketone? Bonus: What is the name of the product and the name of the reactant?
Cyclic thioacetal, replaces =O with single bonds to the ends of a SRS, reactant called a dithiol
What is the effect of adding H2 and RaNi (Raney nickel) to a thioacetal (compound with -SR groups)?
Reduction to alkane, replaces the sulfur with hydrogen
What is the effect of the addition of H2NNH2 to an aldehyde or ketone? Bonus: What is the name of the product and the name of the reactant? What happens when combined with OH-?
Replaces =O with =N-NH2
Reactant is hydrazine and product is hydrazone
If the reaction is combined with OH- it just replaces the =O with two hydrogens.
What is the effect of the addition of H2NNHPh to an aldehyde or ketone? Bonus: What is the product called?
Replaces =O with =NNHPh
Phenylhydrazone
What is the effect of the addition of H2NOH to an aldehyde or ketone? Bonus: What are the product and reactant called?
Replaces =O with =NOH
Reactant is hydroxyl amine and product is oxime
How do you get aldehydes from alcohols? Give some reagents?
oxidize 1* with PCC or Pyridine/CrO3
How do you get aldehydes from carboxylic acids, esters, and acyl chlorides?
reduction with NaBH4, LiAlH(OtBu)3/Et2O,
How do you get ketones from alcohols
oxidize 2* with H2CrO4, PCC, or KMnO4
What are some reagents that will reduce aldehydes to alcohols without adding extra R groups?
LiAlH4 or NaBH4 or Na/EtOH
What are reagents that will reduce aldehydes or ketones to alcohols and add extra R groups?
Grignard(RMgX) or RLi
What are some reagents that will reduce ketones to alcohols without adding extra R groups?
LiAlH4 or NaBH4
What reagents will oxidize aldehydes to carboxylic acids?
(with acid)
KMnO4/OH- or Ag2O/OH
