Chemistry of Benzene, Alcohols, Aldehydes, and Ketones Practice Flashcards

VOCABULARY practice flashcards covering electrophilic aromatic substitution, alcohol reactions, and carbonyl chemistry based on the lecture transcript.

$$F-TEDA-BF_4$$

Adds $F$ to the benzene ring.

$$I_2 / CuCl_2$$

Adds $I$ to the benzene ring.

$$HNO_3 / H_2SO_4$$

Adds $NO_2$ to the benzene ring; note that the ring cannot be deactivated.

$$SO_3 / H_2SO_4$$

Adds $SO_3H$ to the benzene ring.

$$Fe, H_3O^+ / OH^-$$

Turns $NO_2$ into $NH_2$; requires the presence of a $NO_2$ group.

$$OH^- / H_2O$$

Replaces $Cl, Br, \text{ or } I$ with $OH$; requires a strong electron-withdrawing group in the ortho or para position.

$$NH_2^- / NH_3$$

Replaces $Cl, Br, \text{ or } I$ with $NH_2$; requires a halogen and an adjacent ortho-hydrogen.

$$KMnO_4 / H_2O$$

Turns an alkyl chain into $COOH$; requires at least 1 benzylic hydrogen.

$$O_2 / Co(III)$$

Turns $CH_3$ into $COOH$; requires at least 1 benzylic hydrogen.

$$NBS$$

Replaces a benzylic $H$ with $Br$; requires at least 1 benzylic hydrogen and light.

$$H_2, Rh/C$$

Turns the benzene ring into cyclohexane; requires high heat and pressure.

$$H_2, Pd \text{ (or } Pt)$$

Erases all $C=C$ bonds except those in the benzene ring; leaves the carbonyl ($C=O$) group alone.

$$NaBH_4 / H_3O^+$$

Turns an aldehyde into a $1^\text{degree}$ alcohol and a ketone into a $2^\text{degree}$ alcohol; cannot react with acids or esters.

$$LiAlH_4 / H_3O^+$$

Turns aldehydes, esters, and acids into a $1^\text{degree}$ alcohol, and ketones into a $2^\text{degree}$ alcohol.
H2O instead of H3O+: Turns CN into primary amine (CH2-NH2)

$$R'-MgBr / H_3O^+$$

Turns a carbonyl into $OH$ and adds $R'$; cannot be used if $OH$, $NH_2$, or $COOH$ groups are present.

$$1. BH_3, THF / 2. H_2O_2, OH^-$$

Removes a double bond and adds $OH$ on the least substituted carbon; requires an alkene.

$$H_3O^+ \text{ (with Heat)}$$

Turns a $3^\text{degree}$ alcohol into an alkene, and OH + CN = COOH

$$POCl_3 / \text{Pyridine}$$

Turns a $2^\text{degree}$ or $3^\text{degree}$ alcohol into an alkene; requires an adjacent hydrogen.

$$DMP / CH_2Cl_2$$

Turns a $1^\text{degree}$ alcohol into an aldehyde and a $2^\text{degree}$ alcohol into a ketone.

$$CrO_3 / H_3O^+$$

Turns a $1^\text{degree}$ alcohol to $COOH$ and a $2^\text{degree}$ alcohol to a ketone.

$$Na_2Cr_2O_7 / H_2O$$

Turns phenol into a quinone diketone; the ring must be a phenol.

$$PBr_3$$

Replaces an $OH$ group with a $Br$ group; works best on $1^\text{degree}$ and $2^\text{degree}$ alcohols and flips stereochemistry.

$$1. CH_2O / 2. H_3O^+$$

Adds exactly one $CH_2$ group and turns a Grignard reagent into a $1^\text{degree}$ alcohol.

$$DIBAH / H_3O^+$$

Turns an ester into an aldehyde; requires cold temperature ($-78^\text{ degrees C}$).

$$R'_2CuLi$$

Turns an acid chloride into a ketone, or adds $R'$ to the far double-bond carbon.

$$HCN$$

Turns a carbonyl into $OH$ and $CN$ on the same carbon; requires a small amount of base.

$$R''NH_2$$

Turns $C=O$ into $C=NR''$; requires mild acid. If a double bond is next to the $C=O$, the amine attacks the far beta-carbon instead.

$$HNR'_2$$

Turns a carbonyl into an enamine ($N$ adjacent to a double bond); requires an alpha-hydrogen.

Heteroatom Rule (Direct Addition)

If a target has $N$, $O$, or $C$ attached where a $C=O$ used to be, add that molecule directly with $H_3O^+$. Secondary amines form enamines where the double bond shifts to the next carbon.

$$H_2NNH_2 / KOH$$

Turns a carbonyl into $CH_2$; cannot have base-sensitive groups.

$$2 R''OH / \text{Acid Catalyst}$$

Turns a carbonyl into an acetal; this reaction is reversible.

$$HO-CH_2-CH_2-OH / \text{Acid Catalyst}$$

Protects aldehydes first, then ketones; aldehydes react faster because they are less crowded and more reactive.

Cannizzaro Reaction

Uses $OH^- / 2 \text{ Aldehydes} / H_3O^+$ to turn one aldehyde into a $COOH$ acid and the other into an $OH$ alcohol; requires aldehydes with zero alpha-hydrogens.

$$1. NaCN/HCN / 2. H_3O^+$$

Adds $CN$ to the beta position of an alpha,beta-unsaturated carbonyl substrate, then turns it into $COOH$.