ACS ORGANIC CHEMISTRY FINAL EXAM
2025/2026 QUESTIONS AND ANSWERS
What will adding CHBr3 and KOH to an alkene do?
What is the formula used to determine number of stereoisomers in a compound?
2^n
How to determine stereogenic centers in a molecule?
Whenever a compound is bound to 4 different groups! PLEASE don't forget to
check every group!
Which kinds of diols can HIO4 cleave? What does it form?
-It only cleaves 1/2 diols that are cis with respect to each other
-It forms either an aldehyde or a ketone
,How can you create a carboxylic acid from an alkene?
Use KMnO4, acid, and heat; This will cleave the double bond; an aldehyde will be
reduced to a carboxylic acid; a secondary double bond will form a ketone
-Ozonolozysis will cleave it until the aldehyde; KMno4 will cleave it until the
carboxylic acid
Tertiary alcohols are highly resistant to what?
Oxidation
What happens when you take a ketone and you react it with H2 gas and Raney
Nickel?
An alcohol will be formed
What does NaNH2 do with a terminal alkyne?
,Deprotonate the terminal alkyne
Williamson ether synthesis
Pinnacle rearrangement rxn
In chair conformations, what is up and what is down?
Up is wedge; down is dash
What will happen with ethers and alcohols in strong acid?
They will be protonated to become good leaving groups and will be replaced by Br
atom
, What does H2 and Pd/C reduce?
It reduces a C=C faster than a C=O bond; adds two Hs across the double bond
What only reduces a C=O bond but not a C=C bond?
NaBH4 and LAH
Are combustion rxns endo or exo?
Exothermic
What is the IHD (index of hydrogen deficiency?
IHD = 2n+2-H all divided by 2; if N decrease number of H by 1; if halogen
increase number of H by 1; make no changes for O
What is hydrogenation?
Add H2 and Pd/C; add H2
Functional group: alkane
2025/2026 QUESTIONS AND ANSWERS
What will adding CHBr3 and KOH to an alkene do?
What is the formula used to determine number of stereoisomers in a compound?
2^n
How to determine stereogenic centers in a molecule?
Whenever a compound is bound to 4 different groups! PLEASE don't forget to
check every group!
Which kinds of diols can HIO4 cleave? What does it form?
-It only cleaves 1/2 diols that are cis with respect to each other
-It forms either an aldehyde or a ketone
,How can you create a carboxylic acid from an alkene?
Use KMnO4, acid, and heat; This will cleave the double bond; an aldehyde will be
reduced to a carboxylic acid; a secondary double bond will form a ketone
-Ozonolozysis will cleave it until the aldehyde; KMno4 will cleave it until the
carboxylic acid
Tertiary alcohols are highly resistant to what?
Oxidation
What happens when you take a ketone and you react it with H2 gas and Raney
Nickel?
An alcohol will be formed
What does NaNH2 do with a terminal alkyne?
,Deprotonate the terminal alkyne
Williamson ether synthesis
Pinnacle rearrangement rxn
In chair conformations, what is up and what is down?
Up is wedge; down is dash
What will happen with ethers and alcohols in strong acid?
They will be protonated to become good leaving groups and will be replaced by Br
atom
, What does H2 and Pd/C reduce?
It reduces a C=C faster than a C=O bond; adds two Hs across the double bond
What only reduces a C=O bond but not a C=C bond?
NaBH4 and LAH
Are combustion rxns endo or exo?
Exothermic
What is the IHD (index of hydrogen deficiency?
IHD = 2n+2-H all divided by 2; if N decrease number of H by 1; if halogen
increase number of H by 1; make no changes for O
What is hydrogenation?
Add H2 and Pd/C; add H2
Functional group: alkane
