EXAM 3 Flashcards
What does aldehyde reacting with NaBH4 and H3O+ yield?
no rxn
What does aldehyde reacting with LiAlH4 and H3O+ yield?
C bonded to R, OH, and 2H
What does ketone reacting with NaBH4 and H3O+ yield?
C bonded to R, R’, OH, and H
What does ketone reacting with LiAlH4 and H3O+ yield?
C bonded to R, R’, OH, and H
What does carboxylic acid reacting with LiAlH4 and H3O+ yield?
C bonded to OH and R
What does an ester reacting with LiAlH4 and H3O+ yield?
C bonded to OH and R + HOR’
What yields when you react RMgBr with R’ containing double bonded O and H3O+?
R-R’ now containing OH instead of double bonded O
What yields when you react an anhydride with R’‘OH?
ester and carboxylic acid
What yields when you react an anhydride with RNH2?
amide and carboxylic acid
What yields when you react an anhydride with RMgBr?
primary alcohol
What yields when you react an anhydride with [H]?
primary alcohol
Describe alpha substitution reaction
H breaks off carbon next to double bonded O and goes to base, break double bonded O to yield alkene in middle, break this double bond to add E to that C and reform double bonded O
What yields when you react aldehyde with CrO3?
carboxylic acid
What yields when you react aldehyde with NaOH?
deprotonated carboxylic acid
What happens when you react a gringard reagent with carbon dioxide and H3O+?
carboxylic acid
What happens when you react R-C triple bonded with KOH and H3O+?
carboxylic acid
What happens when you react R-C-X with NaCN?
R-C-CN
What happens when you react R-C-CN with LiAlH and H3O+?
C-C-NH2
What happens when you react R-C-CN with KOH and H3O+?
R-carboxylic acid
What happens when you react carboxylic acid with SOCl3?
replace OH with Cl
What happens when you react carboxylic acid with PBr3?
replace OH with Br
What yields when you react R-C=O bonded to good LG with NH3?
replace good leaving group with NH2
What yields when you react R-C=O bonded to good LG with R’OH?
ester
What yields when you react R-C=O bonded to good LG with H2O?
carboxylic acid
What yields when you react R-C=O bonded to good LG with carboxylic acid?
anyhydride
What yields when you react R-C=O bonded to good LG with DiBAlH?
aldehyde
What yields when you react R-C=O bonded to good LG with LiAlH4 and H3O+?
primary alcohol
What yields when you react R-C=O bonded to good LG with R’MgX and H3O+?
C bonded to OH, R and 2R’
What yields when you react R-C=O bonded to good LG with (Cu2R’)Li and H3O+?
C bonded to R, R’, and double bonded O
What yields when you react primary alcohol with Ness Martin?
aldehyde
What yields when you react ester with LiAlH4?
primary alcohol
What yields when you react ester with DiBAlH
aldehyde
What yields when you react ester with Grignard?
C bonded to OH, R, 2R’
What yields when you react ester with R’2CuLi?
C bonded to R, R’, and double bonded O
What yields when you react 2propanol with Dess Martin?
ketone
What yields when you react aldehyde with nucleophile and HA?
C bonded to OH, R, H, and Nu
What yields when you react aldehyde with NuH2?
C bonded to R, H, and double bonded Nu
How do you form imine?
double bonded O and RNH2
How do you form examine?
double bonded O and R2NH2
What is an imine?
carbon molecule with double bond connected to N
What is enamine?
alkene with N single bonded to it
What happens when you react a secondary alcohol with CrO3?
replace alcohol with double bonded O
What happens when you react primary alcohol with CrO3?
form carboxylic acid
What happens when you react secondary alcohol with Dess Martin?
replace alcohol with double bonded O
What happens when you react primary alcohol with Dess Martin?
form aldehyde
What happens when you react ketone with NH2NH2 and KOH?
replace double bonded O with 2 Hs
What happens when you react ketone with 2ROH and H+?
replace double bonded O with 2 OR groups
Describe Witting Rxn
switch O on double bond (stable molecule) with group bonded to R3P (less stable molecule)
How do you synthesize a Witting Rxn?
use nBuLi to bond group on good LG to R3P
What happens when you react ketone with ethanediol (?) and H+?
replace OHs with O and connect them on top of the other 2 Cs (COUNT CARBONS!)
What happens when you react -oate molecule with ethanediol (?), H+, LiAlH4, H2O?
replace ester with alcohol (COUNT CARBONS!)
What kind of addition to you do with Grignard? Where should the double bond be?
1,2 … double bond on ring
What kind of addition to you do with (CuR2)Li? Where should the double bond be?
1,4 … double bond on O
What yields when you react C=C-C=O with NuH?
Nu-C-C=O
What is the suffix on carboxylic acid?
-oic acid
What is the suffix on C-C-NH2 with double bonded O on center C?
-amide
What is the suffix on C-C-X with double bonded O on center C?
-yl halide
What is the suffix on asymmetrical ester?
-oate
What is the suffix on R-C-R’ with double bonded O on center C?
-one
What is the suffix on C-C-H with double bonded O on center C?
-al
What is the suffix on ester with single bonded O replaced by S?
-thioate
What is the suffix on symmetrical ester?
-oic anhydride