List the given functional groups

The groups are: $- ext{OCH}_3,\u00a0- ext{NO}_2,a0- ext{CN},a0- ext{CH}_3,a0- ext{NHCOCH}_3,a0- ext{COR},a0- ext{OH},a0- ext{COOH},a0- ext{Cl}$

Recall the rule for directing effects

In electrophilic aromatic substitution:

• Electron-donating groups are generally ortho/para directing.
• Electron-withdrawing groups are generally meta directing.
• Halogens are an exception: they are deactivating but still ortho/para directing.

Check each group one by one

(i) -text{OCH}_3

Methoxy group donates electron density by resonance.

$- ext{OCH}_3 ext{ is ortho/para directing}$

(ii) -text{NO}_2

Nitro group is strongly electron withdrawing.

$- ext{NO}_2 ext{ is meta directing}$

(iii) -text{CN}

Cyano group is electron withdrawing.

$- ext{CN} ext{ is meta directing}$

(iv) -text{CH}_3

Methyl group donates by hyperconjugation / +I effect.

$- ext{CH}_3 ext{ is ortho/para directing}$

(v) -text{NHCOCH}_3

Acetamido group donates lone pair by resonance from nitrogen.

$- ext{NHCOCH}_3 ext{ is ortho/para directing}$

(vi) -text{COR}

Acyl group is electron withdrawing due to carbonyl.

$- ext{COR} ext{ is meta directing}$

(vii) -text{OH}

Hydroxy group strongly donates by resonance.

$- ext{OH} ext{ is ortho/para directing}$

(viii) -text{COOH}

Carboxyl group is electron withdrawing.

$- ext{COOH} ext{ is meta directing}$

(ix) -text{Cl}

Chlorine is deactivating by $-I$ effect, but donates by resonance, so it is:

$- ext{Cl} ext{ is ortho/para directing}$

Count the meta directing groups

Meta directing groups are: $- ext{NO}_2,a0- ext{CN},a0- ext{COR},a0- ext{COOH}$

Total number: $4$

Compare with stored answer

Stored correct answer = $4$

This matches our derived answer.